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GB834100A - Improvements in the preparation of mixed aldols - Google Patents

Improvements in the preparation of mixed aldols

Info

Publication number
GB834100A
GB834100A GB3346957A GB3346957A GB834100A GB 834100 A GB834100 A GB 834100A GB 3346957 A GB3346957 A GB 3346957A GB 3346957 A GB3346957 A GB 3346957A GB 834100 A GB834100 A GB 834100A
Authority
GB
United Kingdom
Prior art keywords
isobutyraldehyde
hydroxy
aldehyde
aldols
alkali metal
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
GB3346957A
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.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
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 Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to GB3346957A priority Critical patent/GB834100A/en
Publication of GB834100A publication Critical patent/GB834100A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/75—Reactions with formaldehyde

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aldols of the general formula RCH(OH)C(CH3)2CHO, in which R is hydrogen or an alkyl radical containing from 1 to 9 carbon atoms, are prepared by reacting an aliphatic aldehyde of formula RCHO with isobutyraldehyde in a molar ratio of isobutyraldehyde to the other aldehyde of at least 1.1 to 1, at a temperature of from 50 DEG to 90 DEG C. in the presence of an alkali metal carbonate. It is advantageous to use at least a one molar excess of isobutyraldehyde per mol. of other aldehyde. The preferred alkali metal carbonate is potassium carbonate. The catalyst can be used in amounts varying from 2 to 10% based on the weight of isobutyraldehyde and is preferably used as a 20-50% aqueous solution. Examples are given of the reaction of isobutyraldehyde with formaldehyde, acetaldehyde, propionaldehyde and n-butyraldehyde to give hydroxypivalaldehyde,3-hydroxy-2.2-dimethylbutyraldehyde, 3 - hydroxy - 2.2 - dimethylvaleraldehyde and 3 - hydroxy - 2.2 - dimethylhexaldehyde respectively.
GB3346957A 1957-10-26 1957-10-26 Improvements in the preparation of mixed aldols Expired GB834100A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3346957A GB834100A (en) 1957-10-26 1957-10-26 Improvements in the preparation of mixed aldols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3346957A GB834100A (en) 1957-10-26 1957-10-26 Improvements in the preparation of mixed aldols

Publications (1)

Publication Number Publication Date
GB834100A true GB834100A (en) 1960-05-04

Family

ID=10353371

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3346957A Expired GB834100A (en) 1957-10-26 1957-10-26 Improvements in the preparation of mixed aldols

Country Status (1)

Country Link
GB (1) GB834100A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3935274A (en) * 1968-04-24 1976-01-27 Hoechst Aktiengesellschaft Process for the continuous preparation of hydroxypivaldehyde
WO2014155291A1 (en) 2013-03-27 2014-10-02 Pfizer Ireland Pharmaceuticals Process and intermediates for the preparation of pregabalin

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3935274A (en) * 1968-04-24 1976-01-27 Hoechst Aktiengesellschaft Process for the continuous preparation of hydroxypivaldehyde
WO2014155291A1 (en) 2013-03-27 2014-10-02 Pfizer Ireland Pharmaceuticals Process and intermediates for the preparation of pregabalin
EP3216863A1 (en) 2013-03-27 2017-09-13 Pfizer Ireland Pharmaceuticals Process and intermediates for the preparation of pregabalin

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