GB665147A - Improvements in or relating to the preparation of a new unsaturated carbinol - Google Patents

Improvements in or relating to the preparation of a new unsaturated carbinol

Info

Publication number
GB665147A
GB665147A GB7786/49A GB778649A GB665147A GB 665147 A GB665147 A GB 665147A GB 7786/49 A GB7786/49 A GB 7786/49A GB 778649 A GB778649 A GB 778649A GB 665147 A GB665147 A GB 665147A
Authority
GB
United Kingdom
Prior art keywords
acetylene
ether
lithium
derivative
evaporated
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
GB7786/49A
Inventor
Ian Morris Heilbron
Basil Charles Leicester Weedon
Ewart Ray Herbert Jones
Alexander Bertus Arnold Jansen
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.)
Glaxo Laboratories Ltd
Original Assignee
Glaxo Laboratories 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 Glaxo Laboratories Ltd filed Critical Glaxo Laboratories Ltd
Priority to GB7786/49A priority Critical patent/GB665147A/en
Publication of GB665147A publication Critical patent/GB665147A/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
    • C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C45/74—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 combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

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

Abstract

The invention comprises the compound 3-methylocta - 4 : 6 - dien - 1 - yn - 3 - ol represented by the structural formula <FORM:0665147/IV (b)/1> an unsaturated carbinol having the formula C9H12O and having the following characteristics: refractive index ( <FORM:0665147/IV (b)/2> ) 1.5030, light absorption; max. 228 mm , E1 per cent1 cm. 2050, e 28,000. This compound is prepared by reacting crotonylideneacetone with the lithium, sodium or calcium derivative of acetylene in the presence of liquid ammonia. The reaction is preferably carried out at atmospheric pressure using an excess of acetylene. Crotonaldehyde in dry ether is stirred with, in examples (1) the lithium derivative of acetylene formed by adding lithium to a cooled solution of acetylene in liquid ammonia, and (2) the calcium derivative of acetylene similarly prepared. In both examples the ammonia is evaporated and the residue is extracted with ether and water, the mixture being acidified with glacial acelic acid in (2) and the ether layer is dried, after shaking with sodium bicarbonate in (2), the ether is evaporated and the residue distilled to obtain liquids containing 47 per cent and 76 per cent respectively of the desired product.
GB7786/49A 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated carbinol Expired GB665147A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB7786/49A GB665147A (en) 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated carbinol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB7786/49A GB665147A (en) 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated carbinol

Publications (1)

Publication Number Publication Date
GB665147A true GB665147A (en) 1952-01-16

Family

ID=9839691

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7786/49A Expired GB665147A (en) 1949-03-22 1949-03-22 Improvements in or relating to the preparation of a new unsaturated carbinol

Country Status (1)

Country Link
GB (1) GB665147A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746900A (en) * 1953-04-20 1956-05-22 Pfizer & Co C Hypnotic agent and method of making the same
US2815379A (en) * 1954-09-13 1957-12-03 Hoffmann La Roche Alicyclic ketone and intermediates for the preparation thereof
DE1040538B (en) * 1954-09-13 1958-10-09 Hoffmann La Roche Process for the production of new unsaturated alcohols which are distinguished by special odorous properties
DE1041036B (en) * 1954-09-15 1958-10-16 Hoffmann La Roche Process for the production of unsaturated alcohols with special fragrance properties
US4011271A (en) * 1974-04-15 1977-03-08 Hoffmann-La Roche Inc. Preparation and use of magnesium acetylene complex
US4022807A (en) * 1974-04-26 1977-05-10 Hoffmann-La Roche Inc. Vitamin A esters

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2746900A (en) * 1953-04-20 1956-05-22 Pfizer & Co C Hypnotic agent and method of making the same
US2815379A (en) * 1954-09-13 1957-12-03 Hoffmann La Roche Alicyclic ketone and intermediates for the preparation thereof
DE1040538B (en) * 1954-09-13 1958-10-09 Hoffmann La Roche Process for the production of new unsaturated alcohols which are distinguished by special odorous properties
DE1041036B (en) * 1954-09-15 1958-10-16 Hoffmann La Roche Process for the production of unsaturated alcohols with special fragrance properties
US4011271A (en) * 1974-04-15 1977-03-08 Hoffmann-La Roche Inc. Preparation and use of magnesium acetylene complex
US4022807A (en) * 1974-04-26 1977-05-10 Hoffmann-La Roche Inc. Vitamin A esters

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