GB1215073A - Hydroxy aldehydes and derivatives thereof - Google Patents

Hydroxy aldehydes and derivatives thereof

Info

Publication number
GB1215073A
GB1215073A GB8301/68A GB830168A GB1215073A GB 1215073 A GB1215073 A GB 1215073A GB 8301/68 A GB8301/68 A GB 8301/68A GB 830168 A GB830168 A GB 830168A GB 1215073 A GB1215073 A GB 1215073A
Authority
GB
United Kingdom
Prior art keywords
prepared
dialkyl acetal
general formula
hydroxy
acetal
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
GB8301/68A
Inventor
Wilhelm Von Gwinner
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
Publication of GB1215073A publication Critical patent/GB1215073A/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
    • C07D317/10—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 not condensed with other rings
    • C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic

Landscapes

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

Abstract

1,215,073. Hydroxyaldehydes and derivatives thereof. W. VONGWINNER. 20 Feb., 1968 [20 Feb., 1967], No. 8301/68. Heading C2C. Novel 4-hydroxy-2,3-alkenals of the general formula in which R<SP>1</SP> and R<SP>2</SP> are hydrogen, C 1-9 normal alkyl, phenyl or pyridyl, provided that not more than one of R<SP>1</SP> and R<SP>2</SP> is hydrogen, or the alkyl acetal, semicarbazone or N-phenyl hydrazone derivative thereof, are prepared by treating a 4 - hydroxy - 2,3 - alkynal - dialkyl acetal with LiAlH 4 and saponifying the resultant 4- hydroxy-2,3-alkenal-dialkyl acetal having the general formula wherein R is alkyl, with an aqueous solution of a weak acid. The 4-hydroxy-2,3-alkynal-dialkyl acetal may be produced by decomposition of a Grignard reaction product of the general formula wherein X is halogen, with water and said Grignard reaction product may be prepared by treating an aldehyde or ketone of the general formula R<SP>1</SP>R<SP>2</SP>CO, with the Grignard reaction product of propargyl aldehyde dialkyl acetal (prepared by eliminating 2 moles of HBr from 2,3- dibromopropionaldehyde dialkyl acetal) and an alkyl or aryl magnesium halide. Products of the formula are prepared by hydrolysis of the corresponding 4 - bromo - 2,3 - butenal dialkyl acetal, prepared by the action of N-bromosuccinimide on the 2,3-butenal dialkyl acetal, with an aqueous suspension of CaCO 3 and saponifying the product with an aqueous solution of a weak acid. The 2,3-butenal dialkyl acetal is prepared by bromination of a butanol and acetalating the 2-bromo-derivative with an alkanol to form a 2-bromo butanal dialkyl acetal of the general formula and dehydrohalogenating this product. 2,3-Dibromopropionaldehyde is prepared by brominating acrolein.
GB8301/68A 1967-02-20 1968-02-20 Hydroxy aldehydes and derivatives thereof Expired GB1215073A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEN0030034 1967-02-20

Publications (1)

Publication Number Publication Date
GB1215073A true GB1215073A (en) 1970-12-09

Family

ID=7345354

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8301/68A Expired GB1215073A (en) 1967-02-20 1968-02-20 Hydroxy aldehydes and derivatives thereof

Country Status (3)

Country Link
DE (1) DE1618727A1 (en)
FR (2) FR1584471A (en)
GB (1) GB1215073A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106749127A (en) * 2016-12-12 2017-05-31 滕州市悟通香料有限责任公司 One kind synthesis is double（The furyl of 2 methyl 3）The method of disulfide

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63227537A (en) * 1987-03-16 1988-09-21 Shin Etsu Chem Co Ltd Production of omega-substituted-(e)-2-alken-1-al

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106749127A (en) * 2016-12-12 2017-05-31 滕州市悟通香料有限责任公司 One kind synthesis is double（The furyl of 2 methyl 3）The method of disulfide

Also Published As

Publication number Publication date
DE1618727A1 (en) 1971-01-14
FR1584471A (en) 1969-12-26
FR7888M (en) 1970-05-04

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees