GB695529A - Process for the production of crystalline vanillyl amides - Google Patents

Process for the production of crystalline vanillyl amides

Info

Publication number
GB695529A
GB695529A GB24345/51A GB2434551A GB695529A GB 695529 A GB695529 A GB 695529A GB 24345/51 A GB24345/51 A GB 24345/51A GB 2434551 A GB2434551 A GB 2434551A GB 695529 A GB695529 A GB 695529A
Authority
GB
United Kingdom
Prior art keywords
vanillyl
amide
acid
crystalline
amides
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
GB24345/51A
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
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 Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of GB695529A publication Critical patent/GB695529A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Crystalline vanillyl amides are prepared by reacting excess guaiacol with a methylol amide of an aliphatic saturated or unsaturated carboxylic acid having from 6-12 carbon atoms, in the presence of alcoholic hydrogen chloride. The reaction preferably takes place in alcoholic solution at a temperature above 30 DEG C. The vanillyl amide products may be converted into solid alkali salts, for example, by adding a methyl alcohol solution of an alkali hydroxide to a methyl alcohol solution of the crude vanillyl amide and evaporating to dryness. The crystalline sodium salts can be dissolved in water and treated with acids to give pure crystalline vanillyl amides. The general formula of the vanillyl amides is <FORM:0695529/IV (b)/1> in which R is a saturated or unsaturated aliphatic radical with 5-11 carbon atoms. In the examples (a) pelargonic acid methylol amide is reacted with guaiacol in the presence of alcoholic hydrochloric acid to give pelargonic acid vanillyl amide, and (b) undecylenic acid methylol amide is reacted with guaiacol in the presence of methanolic hydrochloric acid to give undecylenic acid vanillyl amide. U.S.A. Specification 1,503,631 is referred to.
GB24345/51A 1950-10-21 1951-10-18 Process for the production of crystalline vanillyl amides Expired GB695529A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE695529X 1950-10-21

Publications (1)

Publication Number Publication Date
GB695529A true GB695529A (en) 1953-08-12

Family

ID=6607484

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24345/51A Expired GB695529A (en) 1950-10-21 1951-10-18 Process for the production of crystalline vanillyl amides

Country Status (1)

Country Link
GB (1) GB695529A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2168976A (en) * 1984-12-20 1986-07-02 Procter & Gamble Amides and compositions thereof having anti-inflammatory activity

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2168976A (en) * 1984-12-20 1986-07-02 Procter & Gamble Amides and compositions thereof having anti-inflammatory activity

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