GB1461150A - Process for the manufacture of y,gamma-unsaturated carbonyl compoounds - Google Patents

Process for the manufacture of y,gamma-unsaturated carbonyl compoounds

Info

Publication number
GB1461150A
GB1461150A GB329376A GB329376A GB1461150A GB 1461150 A GB1461150 A GB 1461150A GB 329376 A GB329376 A GB 329376A GB 329376 A GB329376 A GB 329376A GB 1461150 A GB1461150 A GB 1461150A
Authority
GB
United Kingdom
Prior art keywords
group
ketal
acetal
acid
allyl alcohol
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
GB329376A
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
Publication of GB1461150A publication Critical patent/GB1461150A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation

Landscapes

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

Abstract

1461150 γ,#-Unsaturated carbonyl compounds F HOFFMANN-LA ROCHE & CO 4 July 1974 [5 July 1973] 03293/76 Divided out of 1461149 Heading C2C γ,#-Unsaturated carbonyl compounds of the general formula wherein R<SP>1</SP> represents (a) a saturated hydrocarbon group, (b) an unsaturated hydrocarbon group, (c) an aralkyl group, (d) an aryl group or (e) an oxygen-containing derivative of (a), (b) or (c) in which the oxygen is in the form of a free hydroxy group, an esterified hydroxy group (the esterifying group being an acyloxy group in which the acyl moiety is derived from a lower (C 1 -C 7 ) alkanoic acid or benzoic acid) or an etherified hydroxy group comprising a lower (C 1 -C 7 ) alkoxy or phenyloxy group and in which the oxygen atom is attached to an aliphatic carbon atom on said group, R<SP>2</SP> represents a lower (C 1 -C 8 ) aliphatic (cyclic or acyclic) hydrocarbon group and R<SP>3</SP>, R<SP>4</SP> and R<SP>5</SP> each represent a hydrogen atom or a lower (C 1 -C 8 ) aliphatic (cyclic or acyclic) hydrocarbon group and wherein R<SP>1</SP> and R<SP>2</SP> together can form a carbocyclic ring and R<SP>4</SP> and R<SP>5</SP> to gether can form a carbocyclic ring, are prepared reacting a tertiary allyl alcohol of the general formula with an acetal or ketal of the general formula wherein R<SP>6</SP> represents a straight-chain or branched-chain alkyl group containing from 1 to 20 carbon atoms, in the presence of an acid catalyst system containing a strong acid while maintaining in the reaction mixture a substantial excess of said ketal or acetal as compared with said tertiary allyl alcohol, from 3 to 100 moles of said ketal or acetal being present per mole of said tertiary allyl alcohol. The ketal or acetal and the allyl alcohol may be added incrementally with the acetal or ketal in excess. The acid catalyst system may comprise both a strong acid and a weak acid. An example prepares 6-methyl-5-hepten-2-one. Reference has been directed by the Comptroller to Specification 981,702.
GB329376A 1973-07-05 1974-07-04 Process for the manufacture of y,gamma-unsaturated carbonyl compoounds Expired GB1461150A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US37650073A 1973-07-05 1973-07-05

Publications (1)

Publication Number Publication Date
GB1461150A true GB1461150A (en) 1977-01-13

Family

ID=23485268

Family Applications (2)

Application Number Title Priority Date Filing Date
GB329376A Expired GB1461150A (en) 1973-07-05 1974-07-04 Process for the manufacture of y,gamma-unsaturated carbonyl compoounds
GB2968874A Expired GB1461149A (en) 1973-07-05 1974-07-04 Process for the manufacutre of y,gamma-unsaturated carbonyl compounds

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2968874A Expired GB1461149A (en) 1973-07-05 1974-07-04 Process for the manufacutre of y,gamma-unsaturated carbonyl compounds

Country Status (7)

Country Link
JP (1) JPS5037711A (en)
CH (2) CH597125A5 (en)
DE (1) DE2432351A1 (en)
FR (1) FR2235905B1 (en)
GB (2) GB1461150A (en)
IT (1) IT1015532B (en)
NL (1) NL7409144A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4426321A (en) 1980-08-08 1984-01-17 Givaudan Corporation Odorant alkadienyl ketones, alcohols and oximes

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5754133A (en) * 1980-08-08 1982-03-31 Givaudan & Cie Sa SHINKIHOKOBUTSUSHITSU
DE3361874D1 (en) * 1982-02-03 1986-03-06 Givaudan & Cie Sa Unsaturated oximes, preparation thereof and use thereof as perfume and in the fragment compositions
CN101778810A (en) * 2007-08-08 2010-07-14 帝斯曼知识产权资产管理有限公司 Process for the preparation of (e, e)-farnesyl acetone
JP6476475B2 (en) * 2012-10-08 2019-03-06 ディーエスエム アイピー アセッツ ビー．ブイ．Ｄｓｍ Ｉｐ Ａｓｓｅｔｓ Ｂ．Ｖ． Flavor and aroma mixture (I)
CN110845312A (en) * 2019-11-27 2020-02-28 万华化学集团股份有限公司 Method for preparing methylheptenone

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3453317A (en) * 1962-07-11 1969-07-01 Hoffmann La Roche Unsaturated carbonyl compounds and processes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4426321A (en) 1980-08-08 1984-01-17 Givaudan Corporation Odorant alkadienyl ketones, alcohols and oximes

Also Published As

Publication number Publication date
FR2235905A1 (en) 1975-01-31
NL7409144A (en) 1975-01-07
IT1015532B (en) 1977-05-20
DE2432351A1 (en) 1975-01-23
CH597125A5 (en) 1978-03-31
JPS5037711A (en) 1975-04-08
FR2235905B1 (en) 1978-11-10
GB1461149A (en) 1977-01-13
CH621761A5 (en) 1981-02-27

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee