GB626392A - A process for the manufacture of pentaenes - Google Patents

A process for the manufacture of pentaenes

Info

Publication number
GB626392A
GB626392A GB9199/47A GB919947A GB626392A GB 626392 A GB626392 A GB 626392A GB 9199/47 A GB9199/47 A GB 9199/47A GB 919947 A GB919947 A GB 919947A GB 626392 A GB626392 A GB 626392A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
ether
hydrogenation
yne
methyl
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
GB9199/47A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Priority to GB9199/47A priority Critical patent/GB626392A/en
Publication of GB626392A publication Critical patent/GB626392A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/10—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by etherified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

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

Abstract

Pentaenes are obtained by condensing b -ionone and an ether of 1-hydroxy-3-methyl-6-halogeno-hexene-(2)-yne-(4) in the presence of zinc, cadmium or magnesium, subjecting the ether of 1-hydroxy-3 : 7-dimethyl-7-hydroxy-9 - (21 : 61 : 61 - trimethyl - cyclohexene - (11)-yl) - nonadiene - (2 : 8) - yne - (4) obtained to hydrogenation until one mole of hydrogen has been added to the triple bond of said hydroxy compound and subjecting the hydrogenation product to treatment with a dehydrating agent. Alternatively, the ether of 1-hydroxy-3 : 7-dimethyl - 7 - hydroxy - 9 - (21 : 61 : 61 - tri methyl - cyclohexene - (11) - yl) - nonadine-(2 : 8)-yne-(4) may be subjected to dehydration before hydrogenation. The dehydration may be effected in the presence of a diluent by esterifying with an organic acylating agent and splitting off acid by heating, preferably in the presence of an alkaline agent or by treatment with phosphorous halide and splitting of hydrogen halide from the halogeno compound so formed. The hydrogenation may be effected in the presence of a palladium catalyst. Detailed examples are given. A sample has been furnished under Sect. 2 (5) of Vitamin A-methyl ether made by the alternative method above.
GB9199/47A 1947-04-03 1947-04-03 A process for the manufacture of pentaenes Expired GB626392A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB9199/47A GB626392A (en) 1947-04-03 1947-04-03 A process for the manufacture of pentaenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB9199/47A GB626392A (en) 1947-04-03 1947-04-03 A process for the manufacture of pentaenes

Publications (1)

Publication Number Publication Date
GB626392A true GB626392A (en) 1949-07-14

Family

ID=9867310

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9199/47A Expired GB626392A (en) 1947-04-03 1947-04-03 A process for the manufacture of pentaenes

Country Status (1)

Country Link
GB (1) GB626392A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2726269A (en) * 1955-12-06 Method of making acetylenic carbinols

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2726269A (en) * 1955-12-06 Method of making acetylenic carbinols

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