GB1094238A - Methyl benzylketones - Google Patents
Methyl benzylketonesInfo
- Publication number
- GB1094238A GB1094238A GB43856/65A GB4385665A GB1094238A GB 1094238 A GB1094238 A GB 1094238A GB 43856/65 A GB43856/65 A GB 43856/65A GB 4385665 A GB4385665 A GB 4385665A GB 1094238 A GB1094238 A GB 1094238A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- radical
- hydroxy
- produce
- heating
- Prior art date
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Methyl benzyl ketones of formula <FORM:1094238/C2/1> in which each of R3 and R4 is a hydroxy, esterified hydroxy or tetrahydropyranyl radical or R3 and R4 together represent a C1-C3 alkylenedioxy radical are prepared by mixing a C1-C5 alkyl a -halo propionate, a strong base and a compound of formula <FORM:1094238/C2/2> in which each of R and R1 is a hydroxy, esterified hydroxy, C1-C5 alkoxymethyloxy or tetrahydropyranyl radical or R and R1 together represent a C1-C3 alkylenedioxy or a carbonyldioxy radical, to produce a compound of formula <FORM:1094238/C2/3> in which R2 is a C1-C5 alkyl radical, heating this ester in situ with a solution of an alkali metal hydroxide to saponify the ester and produce the alkali metal salt of the acid, and heating the salt with a strong mineral acid to affect decarboxylation and re-arrangement to produce the required compound. Any carbonyldioxy or alkoxymethyloxy groups present in the starting material are hydrolysed to hydroxy groups during the course of the reaction. The methyl benzyl ketones may be converted to a - methyl - 3,4 - dihydroxyphenylalanine by reacting them in aqueous solution with potassium cyanide and ammonium carbonate to form the corresponding hydantoins and heating the hydantoin in aqueous mineral acid to produce racemic a -methyl-3,4-dihydroxy phenylalanine. The racemic mixture may be resolved into its optically-active components by conventional means. Alternatively if methyl-3,4-methylene-dioxybenzyl ketone is used as starting material the corresponding hydantoin is produced and heated with an aqueous solution of barium hydroxide to give a -methyl-3,4-methylene-dioxyphenylalanine which is treated with red phosphorus and hydrogen iodide to give the racemic 3,4-dihydroxyphenylalanine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40559164A | 1964-10-21 | 1964-10-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1094238A true GB1094238A (en) | 1967-12-06 |
Family
ID=23604323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB43856/65A Expired GB1094238A (en) | 1964-10-21 | 1965-10-15 | Methyl benzylketones |
Country Status (6)
Country | Link |
---|---|
BR (1) | BR6574082D0 (en) |
CH (1) | CH478740A (en) |
DE (2) | DE1793570C3 (en) |
FR (1) | FR1450200A (en) |
GB (1) | GB1094238A (en) |
NL (1) | NL6513089A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4705862A (en) * | 1984-10-05 | 1987-11-10 | Smithkline Beckman Corporation | Chemical processes for 2-(2-halo-3,4-dimethoxybenzyl)-5-(4-methoxyphenyl)oxazolidines |
US4782163A (en) * | 1984-10-05 | 1988-11-01 | Smithkline Beckman Corporation | 2-(2-halo-3,4-dimethoxybenzyl)-5-(4-methoxyphenyl)-oxazolidines |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1186782B (en) * | 1985-10-18 | 1987-12-16 | Montedison Spa | PROCESS FOR THE PREPARATION OF PHENYLPROPANONS |
JP2741069B2 (en) * | 1988-07-08 | 1998-04-15 | 日本石油化学株式会社 | Production of aromatic compounds by a novel oxidation method of aromatic unsaturated compounds |
US7015338B1 (en) | 1999-04-15 | 2006-03-21 | Mars Incorporated | Synthetic methods for preparing procyanidin oligomers |
-
1965
- 1965-10-08 NL NL6513089A patent/NL6513089A/xx unknown
- 1965-10-15 DE DE1793570A patent/DE1793570C3/en not_active Expired
- 1965-10-15 GB GB43856/65A patent/GB1094238A/en not_active Expired
- 1965-10-15 FR FR35124A patent/FR1450200A/en not_active Expired
- 1965-10-15 DE DE19651518037 patent/DE1518037B1/en active Pending
- 1965-10-15 CH CH1423365A patent/CH478740A/en not_active IP Right Cessation
- 1965-10-15 BR BR174082/65A patent/BR6574082D0/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4705862A (en) * | 1984-10-05 | 1987-11-10 | Smithkline Beckman Corporation | Chemical processes for 2-(2-halo-3,4-dimethoxybenzyl)-5-(4-methoxyphenyl)oxazolidines |
US4782163A (en) * | 1984-10-05 | 1988-11-01 | Smithkline Beckman Corporation | 2-(2-halo-3,4-dimethoxybenzyl)-5-(4-methoxyphenyl)-oxazolidines |
Also Published As
Publication number | Publication date |
---|---|
DE1793570B2 (en) | 1973-12-20 |
BR6574082D0 (en) | 1973-08-07 |
CH478740A (en) | 1969-09-30 |
DE1518037B1 (en) | 1970-06-18 |
NL6513089A (en) | 1966-04-22 |
FR1450200A (en) | 1966-05-06 |
DE1793570A1 (en) | 1972-02-24 |
DE1793570C3 (en) | 1974-07-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1283225A (en) | Derivatives of cyclopropane carboxylic acid and process for their preparation | |
DE3460224D1 (en) | Process for the preparation of alkali or alkaline-earth salts of acyloxybenzene-sulfonic acids | |
GB1115750A (en) | Process for the production of cyanoalkylated phenols | |
GB1094238A (en) | Methyl benzylketones | |
GB1102531A (en) | Preparation of azo compounds | |
ES325270A1 (en) | Procedure for the preparation of new substitute phenylacetic acids. (Machine-translation by Google Translate, not legally binding) | |
SE7409248L (en) | PROCEDURE FOR THE PRODUCTION OF ALKALI METAL AND AMMONIUM INSULINES. | |
GB1112825A (en) | An optically active compound and processes for producing it | |
GB1432649A (en) | ||
GB934017A (en) | Color formers for producing yellow dye images by color development | |
ES420665A1 (en) | 7alpha-cyano-17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid ypsilon-lactone and related compounds | |
SE321485B (en) | ||
ES412876A1 (en) | Process for the production of succinylosuccinic diesters | |
GB1022733A (en) | Triaminobenzene | |
GB1103982A (en) | Novel 3,5-seco-a-nor-steroid derivatives | |
ES405646A1 (en) | Procedure for the preparation of new acids 4- (4 bifenilil) -4-hydroxy-butirrics, its esteres or lactonas. (Machine-translation by Google Translate, not legally binding) | |
ES444508A1 (en) | Process for the preparation of phloroglucinol | |
GB1197137A (en) | Substituted Indanones and their Preparation and Reactions | |
GB1069337A (en) | Basically substituted bis-naphthalimides and their production | |
GB1038605A (en) | Process for preparing 2-methoxy-3, 6-dichlorobenzoic acid and product thereof | |
ES278409A1 (en) | Procedure for preparing new amino acids (Machine-translation by Google Translate, not legally binding) | |
ES332381A1 (en) | Procedure for the preparation of steroids. (Machine-translation by Google Translate, not legally binding) | |
ES327502A1 (en) | Procedure for the preparation of new derivatives of isoxazol. (Machine-translation by Google Translate, not legally binding) | |
GB1079534A (en) | Process of manufacture of propanolamine derivatives | |
GB937378A (en) | Production of phenylethylbenzoic acid compounds |