GB1358623A - Process for the manufacture of oxo compounds - Google Patents

Process for the manufacture of oxo compounds

Info

Publication number
GB1358623A
GB1358623A GB2103872A GB2103872A GB1358623A GB 1358623 A GB1358623 A GB 1358623A GB 2103872 A GB2103872 A GB 2103872A GB 2103872 A GB2103872 A GB 2103872A GB 1358623 A GB1358623 A GB 1358623A
Authority
GB
United Kingdom
Prior art keywords
cycloalkyl
cycloalkenyl
group
phenyl
alkyl
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
GB2103872A
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 GB1358623A publication Critical patent/GB1358623A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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
    • C07C403/14—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 doubly-bound oxygen atoms
    • 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
    • C07C45/512—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 a free 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
    • 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)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Duct Arrangements (AREA)

Abstract

1358623 Unsaturated carbonyl compounds; vitamin A aldehydes F HOFFMANN-LA ROCHE & CO AG 5 May 1972 [7 May 1971] 21038/72 Headings C2C and C2V Carbonyl compounds of formula wherein R 1 represents a hydrogen atom or a lower alkyl group and R 2 represents an alkyl or alkenyl group, which may be linked with a cycloalkyl, cycloalkenyl or phenyl group, or a cycloalkyl, cycloalkenyl or phenyl group or R 1 and R 2 are joined together to form a cycloalkyl, cycloalkenyl or phenyl group, and R 3 represents a hydrogen atom or an alkyl or alkenyl group, which may be linked with a cycloalkyl, cycloalkenyl or phenyl group, or a cycloalkyl, cycloalkenyl or phenyl group, and wherein said alkyl, alkenyl, cycloalkyl, cycloalkenyl and phenyl groups can be substituted, if desired, by lower alkyl, lower alkoxy, hydroxy, oxo (which may be ketalized), lower alkanoyl, aroyl, lower alkanoyloxy or aroyloxy are prepared with the aid of a catalyst of the general formula wherein KW represents a hydrocarbon group selected from lower alkyl, cycloalkyl, phenyl and phenyl-(lower alkyl) which may be substituted by lower alkyl, R represents a KW or (KW) 3 -Si group, m stands for 1, 2 or 3 and n stands for zero, 1 or 2 provided that the sum of m and n is 3. Lower signifies C 1-6 . Numerous products are prepared including vitamin A aldehydes. Gyclohex-1-en-1-yl-acetaldehyde is a major by product from 1-ethynyl-1-cyclohexanol (Example 12). 4 - Ethynyl - 4 - hydroxy - 1,1 - ethylenedioxy- 3,5,5-trimethyl-cyclohex-2-ene is prepared from 1,1 -ethylenedioxy-3,5,5-trimethylcyclohex-2-en- 4-one and lithium acetylide.
GB2103872A 1971-05-07 1972-05-05 Process for the manufacture of oxo compounds Expired GB1358623A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH675071A CH589023A5 (en) 1971-05-07 1971-05-07

Publications (1)

Publication Number Publication Date
GB1358623A true GB1358623A (en) 1974-07-03

Family

ID=4314441

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2103872A Expired GB1358623A (en) 1971-05-07 1972-05-05 Process for the manufacture of oxo compounds

Country Status (18)

Country Link
JP (1) JPS5115008B1 (en)
AT (1) AT314489B (en)
AU (1) AU463346B2 (en)
BE (1) BE783055A (en)
BR (1) BR7202834D0 (en)
CA (1) CA996121A (en)
CH (1) CH589023A5 (en)
CS (1) CS166813B2 (en)
DD (1) DD98904A5 (en)
DE (1) DE2222213C3 (en)
FR (1) FR2137550B1 (en)
GB (1) GB1358623A (en)
HU (1) HU166413B (en)
IL (1) IL39368A (en)
NL (1) NL156125C (en)
NO (1) NO134798C (en)
TR (1) TR17320A (en)
ZA (1) ZA723077B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016059152A1 (en) * 2014-10-16 2016-04-21 Dsm Ip Assets B.V. Method for producing specific alpha, beta-unsaturated aldehydes
WO2017046346A1 (en) * 2015-09-17 2017-03-23 Dsm Ip Assets B.V. Production of farnesol
EP3207016B1 (en) * 2014-10-16 2018-08-01 DSM IP Assets B.V. Method for producing specific alpha,beta-unsaturated aldehydes by rearrangement process

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH589023A5 (en) * 1971-05-07 1977-06-30 Hoffmann La Roche

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2863891A (en) * 1955-03-18 1958-12-09 Little Inc A Metal organo-silyl esters
FR1554805A (en) * 1967-11-28 1969-01-24
CH589023A5 (en) * 1971-05-07 1977-06-30 Hoffmann La Roche
GB1409323A (en) * 1972-11-02 1975-10-08 Roche Products Ltd Process for the manufacture of oxo compounds

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016059152A1 (en) * 2014-10-16 2016-04-21 Dsm Ip Assets B.V. Method for producing specific alpha, beta-unsaturated aldehydes
US10029970B2 (en) 2014-10-16 2018-07-24 Dsm Ip Assets B.V. Method for producing specific α, β-unsaturated aldehydes
EP3207016B1 (en) * 2014-10-16 2018-08-01 DSM IP Assets B.V. Method for producing specific alpha,beta-unsaturated aldehydes by rearrangement process
WO2017046346A1 (en) * 2015-09-17 2017-03-23 Dsm Ip Assets B.V. Production of farnesol
US10450250B2 (en) 2015-09-17 2019-10-22 Dsm Ip Assets B.V. Production of farnesol

Also Published As

Publication number Publication date
HU166413B (en) 1975-03-28
AU463346B2 (en) 1975-07-24
BE783055A (en) 1972-11-06
ZA723077B (en) 1973-05-30
FR2137550B1 (en) 1974-07-05
NO134798B (en) 1976-09-06
DE2222213B2 (en) 1976-11-11
CA996121A (en) 1976-08-31
NO134798C (en) 1976-12-15
NL156125C (en) 1980-08-15
BR7202834D0 (en) 1974-08-29
NL7206110A (en) 1972-11-09
JPS5115008B1 (en) 1976-05-13
IL39368A (en) 1975-10-15
AT314489B (en) 1974-04-10
FR2137550A1 (en) 1972-12-29
DD98904A5 (en) 1973-07-12
SU444360A3 (en) 1974-09-25
IL39368A0 (en) 1972-07-26
CH589023A5 (en) 1977-06-30
TR17320A (en) 1975-03-24
AU4197472A (en) 1973-11-08
DE2222213C3 (en) 1984-06-20
NL156125B (en) 1978-03-15
DE2222213A1 (en) 1973-12-20
CS166813B2 (en) 1976-03-29

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
PS Patent sealed [section 19, patents act 1949]
732 Registration of transactions, instruments or events in the register (sect. 32/1977)
PCNP Patent ceased through non-payment of renewal fee