GB1078694A

GB1078694A – Acryloyl phenols
– Google Patents

GB1078694A – Acryloyl phenols
– Google Patents
Acryloyl phenols

Info

Publication number
GB1078694A

GB1078694A
GB348967A
GB348967A
GB1078694A
GB 1078694 A
GB1078694 A
GB 1078694A
GB 348967 A
GB348967 A
GB 348967A
GB 348967 A
GB348967 A
GB 348967A
GB 1078694 A
GB1078694 A
GB 1078694A
Authority
GB
United Kingdom
Prior art keywords
alkyl
dichloro
phenol
reacting
ethylbutyryl
Prior art date
1963-08-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Application number
GB348967A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck and Co Inc

Original Assignee
Merck and Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1963-08-27
Filing date
1964-08-19
Publication date
1967-08-09

1964-08-19
Application filed by Merck and Co Inc
filed
Critical
Merck and Co Inc

1967-08-09
Publication of GB1078694A
publication
Critical
patent/GB1078694A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups

C07C59/40—Unsaturated compounds

C07C59/76—Unsaturated compounds containing keto groups

C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation

C07C45/46—Friedel-Crafts reactions

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton

C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds

C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups

C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton

C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms

C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups

C07C45/75—Reactions with formaldehyde

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates

C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring

C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups

C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides

C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups

Abstract

The invention comprises compounds of the formula wherein R is a hydrogen atom or an alkyl, aryl, aralkyl, cycloalkyl, cycloalkyl-alkyl or C1- 5 -polyhaloalkyl radical, R2 is a hydrogen atom or a C1- 5 alkyl radical, n is 0, 1 or 2 and each X is a halogen atom or a C1- 5 alkyl, C1- 5 alkoxy or trihalomethyl radical or two X radicals on adjacent carbon atoms are joined to form a C3- 4 bivalent hydrocarbon chain, and their preparation by (a) reacting a 4-alkanoylphenol of the formula with paraformaldehyde and the acid addition salt of a di-(C1- 5 alkyl)amine, piperidine or morpholine to produce a 4-[2-(aminomethyl)-alkanoyl] phenol salt of the formula wherein is a di-(C1- 5 alkyl)amino, piperidino or morpholino group and HA is an organic or inorganic acid capable of forming salts with amines, and treating this Mannich salt with a weak base, or (b) reacting the Mannich base with an alkyl halide or dialkyl sulphate to form the corresponding quaternary ammonium salt and treating this with an aqueous solution of a weak base, or (c) reacting the Mannich salt with a mercaptan in the presence of sodium bicarbonate or with a sodium mercaptide followed by treating the product with an aqueous solution of a weak base. 2,3-Dichloro-4-(2-ethylidenebutyryl)phenol is prepared by dehydrobromination of 2,3-dichloro-4-(2-bromo-2-ethylbutyryl)phenol. 3 – Chloro – 4 – butyrylphenol and 2 – butyryl – 5-chlorophenol are prepared by reacting m-chlorophenol with dimethyl sulphate to form 3-chloroanisole, reacting this compound with butyryl chloride in the presence of aluminium chloride to produce a mixture of 3-chloro-4-butyrylanisole and 2 – butyryl – 5 – chloroanisole and hydrolysing these compounds. 2,3-Dichloro – 4 – butyrylpheno and 2,3 – dichloro – 4 -(2-ethylbutyryl)phenol are similarly prepared via 2,3-dichloroanisole. 2,3 – Dichloro – 4 – (2 – bromo – 2 – ethylbutyryl)-phenol is prepared by reacting bromine with 2,3-dichloro-4 -(2-ethylbutyryl)phenol.

GB348967A
1963-08-27
1964-08-19
Acryloyl phenols

Expired

GB1078694A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US30495963A

1963-08-27
1963-08-27

Publications (1)

Publication Number
Publication Date

GB1078694A
true

GB1078694A
(en)

1967-08-09

Family
ID=23178686
Family Applications (2)

Application Number
Title
Priority Date
Filing Date

GB3391964A
Expired

GB1078693A
(en)

1963-08-27
1964-08-19
Preparation of [4-(2-alkylidenealkanoyl)phenoxy]-acetic acids

GB348967A
Expired

GB1078694A
(en)

1963-08-27
1964-08-19
Acryloyl phenols

Family Applications Before (1)

Application Number
Title
Priority Date
Filing Date

GB3391964A
Expired

GB1078693A
(en)

1963-08-27
1964-08-19
Preparation of [4-(2-alkylidenealkanoyl)phenoxy]-acetic acids

Country Status (9)

Country
Link

AT
(1)

AT260906B
(en)

BR
(1)

BR6462120D0
(en)

CH
(1)

CH467231A
(en)

ES
(1)

ES303682A1
(en)

FI
(1)

FI43873B
(en)

FR
(1)

FR1568709A
(en)

GB
(2)

GB1078693A
(en)

NL
(1)

NL6409963A
(en)

SE
(1)

SE333937B
(en)

1964

1964-08-12
AT
AT693464A
patent/AT260906B/en
active

1964-08-19
GB
GB3391964A
patent/GB1078693A/en
not_active
Expired

1964-08-19
GB
GB348967A
patent/GB1078694A/en
not_active
Expired

1964-08-22
ES
ES0303682A
patent/ES303682A1/en
not_active
Expired

1964-08-25
FI
FI180964A
patent/FI43873B/fi
active

1964-08-26
CH
CH1117564A
patent/CH467231A/en
unknown

1964-08-26
SE
SE1027664A
patent/SE333937B/xx
unknown

1964-08-26
BR
BR16212064A
patent/BR6462120D0/en
unknown

1964-08-26
FR
FR1568709D
patent/FR1568709A/fr
not_active
Expired

1964-08-27
NL
NL6409963A
patent/NL6409963A/xx
unknown

Also Published As

Publication number
Publication date

ES303682A1
(en)

1965-05-16

GB1078693A
(en)

1967-08-09

NL6409963A
(en)

1965-03-01

CH467231A
(en)

1969-01-15

AT260906B
(en)

1968-03-25

SE333937B
(en)

1971-04-05

FR1568709A
(en)

1969-05-30

FI43873B
(en)

1971-03-31

BR6462120D0
(en)

1973-08-14

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