GB1422684A - Methylfumaraldehyde monoacetals and process for making them - Google Patents

Methylfumaraldehyde monoacetals and process for making them

Info

Publication number
GB1422684A
GB1422684A GB2510773A GB2510773A GB1422684A GB 1422684 A GB1422684 A GB 1422684A GB 2510773 A GB2510773 A GB 2510773A GB 2510773 A GB2510773 A GB 2510773A GB 1422684 A GB1422684 A GB 1422684A
Authority
GB
United Kingdom
Prior art keywords
methyl
acetal
fumaraldehyde
dimethylpropylene
give
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
GB2510773A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB1422684A publication Critical patent/GB1422684A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Abstract

1422684 Cyclic fumaraldehyde monoacetals; retinal BADISCHE ANILIN- & SODA-FABRIK AG 25 May 1973 [26 May 1972] 25107/73 Headings C2C and C2V The invention comprises cyclic methyl fumaraldehyde mono acetals of the general formula in which R<SP>1</SP> and R<SP>2</SP> are different and denote hydrogen or methyl and R<SP>3</SP> and R<SP>4</SP> together denote a propylene group which may carry C 1 -C 4 alkyl substituents. They may be prepared by oxidizing a methyl derivative of the corresponding hydroxy acetal of formula with a solution of sulphuric acid and chromic acid in acetone. Examples are given of the preparation of 2-methyl-fumaraldehyde-1-(2<SP>1</SP>,2- dimethylpropylene)acetal; 2-methyl-fumaraldehyde - 1 - (1<SP>1</SP>,3<SP>1</SP> - propylene) - acetal; 2 - methylfumaraldehyde - 1 - (2<SP>1</SP>,4<SP>1</SP> - pentylene) - acetal; and 3 - methyl - furmaraldehyde - 1 - (2<SP>1</SP>,2<SP>1</SP>- dimethylpropylene-acetal. The starting material for the first of these compounds is made by treating γ-formyl crotyl acetate with neopentyl glycol to give 2-methyl-4-acetoxy-but-2-en-1- al-(2<SP>1</SP>,2<SP>1</SP>-dimethylpropylene) acetal which is reacted with sodium methylate to give the required hydroxy compound. The cyclic 3- methyl fumaraldehyde monoacetals may be reacted with the ylid of a #-ionylidene ethyl triphenylphosphonium salt, followed by hydrolysis to give retinal.
GB2510773A 1972-05-26 1973-05-25 Methylfumaraldehyde monoacetals and process for making them Expired GB1422684A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19722225612 DE2225612C2 (en) 1972-05-26 1972-05-26 Cyclic methyl-fumaric dialdehyde monoacetals and process for their preparation

Publications (1)

Publication Number Publication Date
GB1422684A true GB1422684A (en) 1976-01-28

Family

ID=5845937

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2510773A Expired GB1422684A (en) 1972-05-26 1973-05-25 Methylfumaraldehyde monoacetals and process for making them

Country Status (5)

Country Link
JP (1) JPS5523829B2 (en)
CH (1) CH579068A5 (en)
DE (1) DE2225612C2 (en)
FR (1) FR2189359B1 (en)
GB (1) GB1422684A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4256643A (en) * 1978-09-30 1981-03-17 Basf Aktiengesellschaft 3-Chloro-3-methyl-butane-1,4-dial-bis-acetals and 3-methyl-but-2-ene-1,4-dial-bis-acetals, a process for the preparation of these compounds and their use
US4804786A (en) * 1986-01-25 1989-02-14 Basf Aktiengesellschaft Preparation of 4-monoacetals of 2-methylbut-2-ene-1,4-dial

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2917413A1 (en) * 1979-04-28 1980-11-06 Basf Ag A PROCESS FOR THE PREPARATION OF CYCLIC ACETALS FROM TRANS-4-CHLORO-3-METHYL-2-BUTEN-1-AL AND TRANS-3-METHYL-2-BUTEN-1,4-DIAL-1-MONOACETALS
DE3617409A1 (en) * 1986-05-23 1987-11-26 Basf Ag METHOD FOR PRODUCING 4-ACETALS OF BUTENDIAL (1,4) AND NEW ACETALS OF BUTENDIAL (1,4)
DE4106907A1 (en) * 1991-03-05 1992-09-10 Basf Ag METHOD FOR PRODUCING 3-ALKOXYCARBONYLPROPENALEN AND 3-DIALKOXYMETHYLPROPENALEN

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4256643A (en) * 1978-09-30 1981-03-17 Basf Aktiengesellschaft 3-Chloro-3-methyl-butane-1,4-dial-bis-acetals and 3-methyl-but-2-ene-1,4-dial-bis-acetals, a process for the preparation of these compounds and their use
US4804786A (en) * 1986-01-25 1989-02-14 Basf Aktiengesellschaft Preparation of 4-monoacetals of 2-methylbut-2-ene-1,4-dial

Also Published As

Publication number Publication date
CH579068A5 (en) 1976-08-31
FR2189359B1 (en) 1976-06-11
DE2225612A1 (en) 1973-12-20
JPS4954383A (en) 1974-05-27
JPS5523829B2 (en) 1980-06-25
FR2189359A1 (en) 1974-01-25
DE2225612C2 (en) 1982-07-01

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Legal Events

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

Effective date: 19920525