GB580921A - Improvements in the synthesis of secondary and tertiary ethinyl-carbinols - Google Patents

Improvements in the synthesis of secondary and tertiary ethinyl-carbinols

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Publication number
GB580921A
GB580921A GB14291/42A GB1429142A GB580921A GB 580921 A GB580921 A GB 580921A GB 14291/42 A GB14291/42 A GB 14291/42A GB 1429142 A GB1429142 A GB 1429142A GB 580921 A GB580921 A GB 580921A
Authority
GB
United Kingdom
Prior art keywords
added
acetylene
ether
ethylene glycol
potassium hydroxide
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
GB14291/42A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB14291/42A priority Critical patent/GB580921A/en
Publication of GB580921A publication Critical patent/GB580921A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes

Landscapes

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

Abstract

Secondary and tertiary ethinyl carbinols are prepared by reaction of acetylenic hydrocarbons with aldehydes or ketones in presence of an alkali metal hydroxide and a solvent of the formula <FORM:0580921/IV/1> where R1 and R2 are alkyl groups, and R3, R4, R5 and R6 hydrogen atoms or alkyl groups. Solvents specified are ethylene glycol dibutyl or ethyl-butyl ether, and propylene glycol diethyl ether. Potassium hydroxide may be added to an excess of the solvent while cooling to 5 DEG C. or below, acetylene and the carbonyl compound then being added alternately in portions. Substituted acetylenes such as amyl or phenyl acetylene may be added mixed with the carbonyl compound. Ethylene glycol ethylbutyl ether is prepared by adding the monoethyl ether to a suspension of sodium in toluene, and then adding butyl bromide. In examples: (1) potassium hydroxide is added to ethylene glycol ethyl butyl ether to produce a gelatinous complex, acetylene and acetone added alternately and, when reaction is complete, the product saturated with CO2, and worked up to give methyl butinol and tetramethyl butine diol; (2) phenyl acetylene and acetone in the same solvent are treated with potassium hydroxide yielding 1-phenyl-3-methyl-butinol-3.
GB14291/42A 1941-04-18 1941-04-18 Improvements in the synthesis of secondary and tertiary ethinyl-carbinols Expired GB580921A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB14291/42A GB580921A (en) 1941-04-18 1941-04-18 Improvements in the synthesis of secondary and tertiary ethinyl-carbinols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB14291/42A GB580921A (en) 1941-04-18 1941-04-18 Improvements in the synthesis of secondary and tertiary ethinyl-carbinols

Publications (1)

Publication Number Publication Date
GB580921A true GB580921A (en) 1946-09-25

Family

ID=10038514

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14291/42A Expired GB580921A (en) 1941-04-18 1941-04-18 Improvements in the synthesis of secondary and tertiary ethinyl-carbinols

Country Status (1)

Country Link
GB (1) GB580921A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102476978A (en) * 2010-11-24 2012-05-30 杨朝辉 Novel synthetic method preparing alkynol compound from acetylene

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102476978A (en) * 2010-11-24 2012-05-30 杨朝辉 Novel synthetic method preparing alkynol compound from acetylene
CN102476978B (en) * 2010-11-24 2015-04-08 杨朝辉 Novel synthetic method preparing alkynol compound from acetylene

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