GB1094238A - Methyl benzylketones - Google Patents

Methyl benzylketones

Info

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
Application number
GB43856/65A
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.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1094238A publication Critical patent/GB1094238A/en
Expired legal-status Critical Current

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.
GB43856/65A 1964-10-21 1965-10-15 Methyl benzylketones Expired GB1094238A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (2)

* Cited by examiner, † Cited by third party
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

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