GB1363170A – Process for the manufacture of ethers
– Google Patents
GB1363170A – Process for the manufacture of ethers
– Google Patents
Process for the manufacture of ethers
Info
Publication number
GB1363170A
GB1363170A
GB5797772A
GB5797772A
GB1363170A
GB 1363170 A
GB1363170 A
GB 1363170A
GB 5797772 A
GB5797772 A
GB 5797772A
GB 5797772 A
GB5797772 A
GB 5797772A
GB 1363170 A
GB1363170 A
GB 1363170A
Authority
GB
United Kingdom
Prior art keywords
butoxy
methylmorphinan
didehydro
epoxy
butyl
Prior art date
1971-12-16
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
GB5797772A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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.)
1971-12-16
Filing date
1972-12-15
Publication date
1974-08-14
1972-12-15
Application filed by F Hoffmann La Roche AG
filed
Critical
F Hoffmann La Roche AG
1974-08-14
Publication of GB1363170A
publication
Critical
patent/GB1363170A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D489/00—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
C07D489/02—Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
C07C41/01—Preparation of ethers
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 – C07D219/00
C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 – C07D219/00 condensed with carbocyclic rings or ring systems
C07D221/22—Bridged ring systems
C07D221/28—Morphinans
Abstract
1363170 Dimethylformamide acetals and a process for ethers F HOFFMANN-LA ROCHE & CO AG 15 Dec 1972 [16 Dec 1971] 57977/72 Heading C2C The invention comprises reacting a phenol with N,N-dimethylformamide di-tert.-butyl acetal (obtained substantially pure by the interaction of the dimethyl acetal with tert.-butanol in the presence of acid) under basic conditions to give tert.-butyl aryl ethers. Examples of phenolic hydrocarbons which can be used in the process are phenol, naphthol, 3-hydroxy-N-formylmorphinan, 3-hydroxymorphinan, morphine, o-, m- and p-cresol, p-aminophenol, o-nitrophenol, 2,4,6 – trinitrophenol, p – acetamidophenol, thymol, 2,6 – di – t – butyl – 4 – methylphenol, 2 – hydroxy – 4 – isopropyltoluene, guaiacol, eugenol, pyrocatechol, resorcinol, hydroquinone, 2,4,6 – trinitroresorcinol, pyrogallol, phloroglucinol and o-, m- and p-bromophenol. Examples of t-butyl aryl ethers obtained are (+)-3-t-butoxy-N-methylmorphinan and its D-tartrate hydrate, (- )-3-t-butoxy-N- methylmorphinan and its L – tartrate hydrate, (+) – 3 – t – butoxymorphinan and its D-tartrate, 3 – t – butoxy – 7,8 – didehydro – 4,5α – epoxy – 17- methylmorphinan – 6α – ol and its D – tartrate diethanolate, t – butyl phenyl ether, t – butyl 1- naphthyl ether, o-, m- and p – t – butoxytoluene, 1 – t – butoxy – 2 – nitrobenzene, 1 – t – butoxy – 3- nitrobenzene, 1 – t – butoxy – 4 – nitrobenzene, 1- t – butoxy – 2,4,6 – trinitrobenzene, 1 – bromo – 2- t – butoxybenzene, 1 – bromo – 3 – t – butoxybenzene, 1 – bromo – 4 – t – butoxybenzene, 1,2 – di – tbutoxybenzene, 1 – t – butoxy – 2 – methoxybenzene, 1,3 – di – t – butoxy – 4 – n – hexylbenzene, 1,4 – dit – butoxybenzene, 1,2,3 – tri – t – butoxybenzene, 1,3,5 – tri – t – butoxybenzene, p – t – butoxyacetanilide, (+) – 3 – t – butoxy – N – formylmorphinan, 3 – t – butoxy – 7,8 – didehydro – 4,5α- epoxy – 17 – methylmorphinan – 6α – ol trans – 3- dimethylamino – 2 – propenoic acid ester and 3 – t – butoxy – 7,8 – didehydro – 4,5α – epoxy – 17- methylmorphinan – 6α – ol dimethylcarbamate. The following compounds are also prepared: (+) – 3 – methoxymorphinan, ( + ) – 3 – hydroxymorphinan, (+) – 3 – hydroxy – N – formylmorphinan, O
GB5797772A
1971-12-16
1972-12-15
Process for the manufacture of ethers
Expired
GB1363170A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US20895271A
1971-12-16
1971-12-16
Publications (1)
Publication Number
Publication Date
GB1363170A
true
GB1363170A
(en)
1974-08-14
Family
ID=22776732
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB5797772A
Expired
GB1363170A
(en)
1971-12-16
1972-12-15
Process for the manufacture of ethers
Country Status (5)
Country
Link
JP
(1)
JPS4867231A
(en)
CH
(1)
CH580554A5
(en)
DE
(1)
DE2261457A1
(en)
FR
(1)
FR2163556B1
(en)
GB
(1)
GB1363170A
(en)
1972
1972-12-11
CH
CH1796672A
patent/CH580554A5/xx
not_active
IP Right Cessation
1972-12-12
JP
JP12401572A
patent/JPS4867231A/ja
active
Pending
1972-12-13
FR
FR7244320A
patent/FR2163556B1/fr
not_active
Expired
1972-12-15
GB
GB5797772A
patent/GB1363170A/en
not_active
Expired
1972-12-15
DE
DE19722261457
patent/DE2261457A1/en
active
Pending
Also Published As
Publication number
Publication date
JPS4867231A
(en)
1973-09-13
FR2163556B1
(en)
1976-06-04
CH580554A5
(en)
1976-10-15
FR2163556A1
(en)
1973-07-27
DE2261457A1
(en)
1973-06-20
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Legal Events
Date
Code
Title
Description
1974-12-27
PS
Patent sealed
1979-07-18
PCNP
Patent ceased through non-payment of renewal fee
