GB1246206A

GB1246206A – Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters
– Google Patents

GB1246206A – Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters
– Google Patents
Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters

Info

Publication number
GB1246206A

GB1246206A
GB23985/69A
GB2398569A
GB1246206A
GB 1246206 A
GB1246206 A
GB 1246206A
GB 23985/69 A
GB23985/69 A
GB 23985/69A
GB 2398569 A
GB2398569 A
GB 2398569A
GB 1246206 A
GB1246206 A
GB 1246206A
Authority
GB
United Kingdom
Prior art keywords
ethylide
alkyl
phosphonic acid
epoxypropyl
cis
Prior art date
1968-05-15
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
GB23985/69A
Inventor
Burton Grant Christensen
Raymond Armond Firestone
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.)
1968-05-15
Filing date
1969-05-12
Publication date
1971-09-15

1969-05-12
Application filed by Merck and Co Inc
filed
Critical
Merck and Co Inc

1971-09-15
Publication of GB1246206A
publication
Critical
patent/GB1246206A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 – C07C337/00

C07C381/12—Sulfonium compounds

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 – C07C337/00

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/02—Phosphorus compounds

C07F9/28—Phosphorus compounds with one or more P—C bonds

C07F9/535—Organo-phosphoranes

C07F9/5352—Phosphoranes containing the structure P=C-

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/02—Phosphorus compounds

C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom

C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms

C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring

C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof

Abstract

1,246,206. (Cis 1,2 – epoxypropyl) – phosphonic acid and intermediates therefor. MERCK & CO. Inc. 12 May, 1969 [15 May, 1968], No. 23985/69. Heading C2C. (Cis-1,2-epoxypropyl)-phosphonic acid and its salts and esters are obtained by treating a formyl phosphonate, e.g. a compound in which R is a C 1 -C 5 alkyl, C 2 -C 5 alkenyl, aryl, or aralkyl radical with an ethylide which is substituted at the methylene carbon by an appropriate leaving group, i.e. a compound M#-CH#-CH 3 wherein M+ is the leaving group, e.g. a di-(C 1 -C 5 )- alkoxy phosphinyl, di-(C 1 -C 5 ) alkyl or diaryl sulphonium, tri-(C 1 -C 5 )-alkyl- (or triaryl) – ammonium, di-(C 1 -C 5 )-alkyl sulphoxonium, tri-(C 1 -C 5 )-alkyl phosphonium or triaryl phosphonium cation. The process is suitably conducted in a solvent, e.g. an ether or dimethylsulphoxide, and the ethylide reactant may be prepared in situ in the solvent and the formyl phosphonate then added to the solution. When the products are esters they may be converted to the free (cis-1,2-epoxypropyl)-phosphonic acid, e.g. by hydrolysis with a mineral acid, hydrogenolysis, or treatment with trimethylchlorosilane followed by -aqueous hydrolysis. The phosphonic acid may then be converted to a salt, e.g. an alkali metal or alkaline earth metal salt, especially the calcium or disodium salt, by treatment with an aqueous solution of an appropriate base. Diethyl sulphoxonium ethylide is obtained by reacting diethyl sulphoxide with ethyl iodide in solution at 100-110 C. to form triethylsulphoxonium iodide and then treating the latter with sodium methylsulphonyl methylide in dimethyl sulphoxide. Triethylammonium ethylide is obtained by adding tetraethylammonium bromide in ether to an ethereal solution of phenyl lithium at 25 C. and decanting the supernatant liquid. Diethylsulphonium ethylide is obtained by reacting diethyl sulphide with ethyl bromide to form triethylsulphonium bromide and then treating the latter with an equivalent of sodium methyl sulphonyl methylide in dimethylsulphoxide.

GB23985/69A
1968-05-15
1969-05-12
Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters

Expired

GB1246206A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US72941568A

1968-05-15
1968-05-15

Publications (1)

Publication Number
Publication Date

GB1246206A
true

GB1246206A
(en)

1971-09-15

Family
ID=24930926
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB23985/69A
Expired

GB1246206A
(en)

1968-05-15
1969-05-12
Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters

Country Status (8)

Country
Link

BE
(1)

BE733047A
(en)

CH
(1)

CH537954A
(en)

DE
(1)

DE1924264A1
(en)

ES
(1)

ES367106A1
(en)

GB
(1)

GB1246206A
(en)

IL
(1)

IL32135A0
(en)

NL
(1)

NL6905269A
(en)

SE
(1)

SE362884B
(en)

1969

1969-04-01
SE
SE04616/69A
patent/SE362884B/xx
unknown

1969-04-03
NL
NL6905269A
patent/NL6905269A/xx
unknown

1969-05-01
IL
IL32135A
patent/IL32135A0/en
unknown

1969-05-12
DE
DE19691924264
patent/DE1924264A1/en
active
Pending

1969-05-12
ES
ES367106A
patent/ES367106A1/en
not_active
Expired

1969-05-12
GB
GB23985/69A
patent/GB1246206A/en
not_active
Expired

1969-05-14
CH
CH743069A
patent/CH537954A/en
not_active
IP Right Cessation

1969-05-14
BE
BE733047D
patent/BE733047A/xx
unknown

Also Published As

Publication number
Publication date

SE362884B
(en)

1973-12-27

IL32135A0
(en)

1969-07-30

DE1924264A1
(en)

1970-01-22

NL6905269A
(en)

1969-11-18

ES367106A1
(en)

1971-06-16

CH537954A
(en)

1973-06-15

BE733047A
(en)

1969-11-14

Similar Documents

Publication
Publication Date
Title

DE59906738D1
(en)

2003-10-02

Process for the preparation of phosphinic acid esters

GB1449394A
(en)

1976-09-15

Fungicides

GB1267016A
(en)

1972-03-15

ATE279421T1
(en)

2004-10-15

METHOD FOR PRODUCING ETHANE-1,2-BIS(ALKYLPHOSPHIC ACIDS)

JPS57168954A
(en)

1982-10-18

Inorganic powder modified with organic phosphate compound

ATE146478T1
(en)

1997-01-15

METHOD FOR PRODUCING LITHIUM DIARYL PHOSPHIDES AND ALKYL DERIVATIVES THEREOF

GB1171155A
(en)

1969-11-19

Improvements in or relating to Cycloalkane Derivatives and the manufacture thereof

GB1246206A
(en)

1971-09-15

Preparation of (cis-1,2-epoxypropyl)phosphonic acid and its salts and esters

DE59906740D1
(en)

2003-10-02

Process for the preparation of phosphonous esters

GB1525486A
(en)

1978-09-20

Phosphonomethyl glycine derivatives

GB1204285A
(en)

1970-09-03

Process for the production of hydroxyphenylakyl phosphoryl or thiophosphoryl compounds

US3420917A
(en)

1969-01-07

Tris(disubstituted phosphenyl ethyl) phosphine oxides

ES482903A1
(en)

1980-04-16

Process for the preparation of phosphoric acid triesters and compounds produced by this process.

NO834275L
(en)

1984-05-25

COATED PARTICULATED FILLINGS

GB1429039A
(en)

1976-03-24

Dialkylphosphinyl compounds

GB673871A
(en)

1952-06-11

Improvements in or relating to process for the manufacture of tetraalkyllead compounds

US3641065A
(en)

1972-02-08

Method for the preparation of (cis-1 2 – epoxypropyl)phosphonic acid derivatives

GB745161A
(en)

1956-02-22

Lubricating compositions

Van den Berg et al.

1971

Stereochemistry of a Michaelis–Arbusov reaction: alkylation of optically active ethyl trimethylsilyl phenylphosphonite with retention of configuration

GB1244910A
(en)

1971-09-02

Preparation of (cis-1,2-epoxypropyl)phosphonic acid, derivatives thereof and intermediates therefor

GB1422898A
(en)

1976-01-28

Large ring gold-sulphur-phosphine chelates and anti-arthritic compositions comprising them

GB707961A
(en)

1954-04-28

Improvements in or relating to the production of organic phosphorus compounds

GB1239986A
(en)

1971-07-21

(-) (cis-1,2-epoxypropyl) phosphonic acid derivatives

US3065273A
(en)

1962-11-20

Method for preparing biphosphines

GB1480391A
(en)

1977-07-20

Aromatic and aralkyl phosphonates process for their manufacture and process for flameproofing organic fibre materials by the transfer process

Download PDF in English