GB651445A - Improvements relating to the preparation of di-acid bases - Google Patents

Improvements relating to the preparation of di-acid bases

Info

Publication number
GB651445A
GB651445A GB24152/48A GB2415248A GB651445A GB 651445 A GB651445 A GB 651445A GB 24152/48 A GB24152/48 A GB 24152/48A GB 2415248 A GB2415248 A GB 2415248A GB 651445 A GB651445 A GB 651445A
Authority
GB
United Kingdom
Prior art keywords
alkyl
diacetyl
dimethoxy
diphenyl ether
phenylacetyl
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
GB24152/48A
Inventor
Frederick Charles Copp
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation Ltd
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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB24152/48A priority Critical patent/GB651445A/en
Publication of GB651445A publication Critical patent/GB651445A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/14—Adipic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Bases of the formula <FORM:0651445/IV (b)/1> where R1 and R2 are hydrogen, alkyl or alkenyl, or form a ring with the nitrogen atom, A and B are alkyl, aryl or aralkyl, and C and/or D or any aromatic rings in A and/or B may contain alkyl or alkoxy substituents (other than an alkyl group ortho to the methylene group), are obtained from ketones <FORM:0651445/IV (b)/2> by known methods. Specified methods are (1) conversion into oximes or hydrazones, followed by catalytic reduction, preferably in the presence of ammonia; (2) catalytic reduction in the presence of ammonia; (3) catalytic reduction in the presence of a primary or secondary amine (not suitable when A and/or B is aryl); (4) reduction to the dicarbinols, treatment with hydrogen bromide to give the dibromides and reaction of these with ammonia or a primary or secondary amine (not suitable when A and/or B is aralkyl). In the case of (1) and (2) compounds are formed where R1 and R2 are both hydrogen, and in these and other cases, the free hydrogen atoms attached to the nitrogen atoms may be replaced by alkyl groups, e.g. by treatment with formic acid and formaldehyde. The bases may be converted into salts with acids, e.g. hydrochloric, but the formation of quaternary salts is p covered by Specification 651,433. Examples are given of various methods for obtaining the products, including purification via the picrate. The preparation of the dioximes of the following substituted diphenyl ethers is described: 4 : 41-dipropionyl-, 4 : 4-dibutyryl0, 4 : 41-divaleryl-, 4 : 41-dicaproyl-, 4 : 41-diheptoyl-, 4 : 41-dioctanoyl-, 4 : 41-di-p-toluyl-, 2-methoxy-41 : 5-diacetyl-, 2 : 21-dimethoxy-5 : 51-diacetyl- and 2 : 21-dimethoxy-5 : 51-di-phenylacetyl-, and also the dihydrazone of 4 : 41-diacetyl-diphenyl ether. Diacyl-diphenyl ethers are obtained by condensing diphenyl ether (or alkyl or alkoxy substitution derivatives thereof) with acyl chlorides in the presence of aluminium chloride. The following substituted diphenyl ethers are mentioned: 4 : 41-dipropionyl-, 4 : 41-dibutyryl-, 4 : - divaleryl-, 4 : 41 - dicaproyl-, 4 : 41 - diheptoyl-, 4 : 41-dioctanoyl-, 4 : 41-di-p-toluyl-, 4 : 41 - di - phenylacetyl-, 2 - methoxy - 41 : 5 - dibenzoyl-, 2 : 21 - dimethoxy - 5 : 51 - diacetyl-, and 2 : 21 - dimethoxy - 5 : 51 - di - phenylacetyl. Dicarbinols of the formula <FORM:0651445/IV (b)/3> where A, B, C and D are defined above, are obtained by reduction of the corresponding diketones. The preparation of 4 : 41-bis-(a -hydroxyethyl)-diphenyl ether and 4 : 41-bis-(a -hydroxy-hexyl)-diphenyl ether is described.
GB24152/48A 1948-09-14 1948-09-14 Improvements relating to the preparation of di-acid bases Expired GB651445A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB24152/48A GB651445A (en) 1948-09-14 1948-09-14 Improvements relating to the preparation of di-acid bases

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB24152/48A GB651445A (en) 1948-09-14 1948-09-14 Improvements relating to the preparation of di-acid bases

Publications (1)

Publication Number Publication Date
GB651445A true GB651445A (en) 1951-04-04

Family

ID=10207210

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24152/48A Expired GB651445A (en) 1948-09-14 1948-09-14 Improvements relating to the preparation of di-acid bases

Country Status (1)

Country Link
GB (1) GB651445A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3182085A (en) * 1961-03-29 1965-05-04 Dow Chemical Co Products prepared from the reaction of halomethylated diphenyl oxide and amines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3182085A (en) * 1961-03-29 1965-05-04 Dow Chemical Co Products prepared from the reaction of halomethylated diphenyl oxide and amines

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