Acetic Acid → Methyl 3-oxo-6-heptenoate

HRID 616289Notes

Reaction equation

HRID 616289 reaction equation
[CH2:1]([CH2:4][C:5](=[O:7])[CH3:6])[CH:2]=[CH2:3].[C:8]([OH:11])(=[O:10])C.[H-].[Na+].[CH3:14]COCC>>[CH3:14][O:11][C:8](=[O:10])[CH2:6][C:5](=[O:7])[CH2:4][CH2:1][CH:2]=[CH2:3]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 79895-Hexene-2-oneHCID 24758Sodium hydride

Product 1

HCID 366065Methyl 3-oxo-6-heptenoate

Procedure

A solution of allylacetone (40 g; 0.42 mol) in 110 ml of ether was added dropwise to the stirred mixture during about 5 hours. The mixture was allowed to stand overnight at room temperature, and was stirred for 1 hour under refluxing, and then 50 ml of acetic acid was added to the mixture to decompose the unreacted sodium hydride. The reaction mixture was treated by the conventional method and the remained oily material was distilled to obtain 50 g of 3-oxo-6-heptenoic acid methyl ester.

Workup

  1. temperatureunder refluxing
  2. additionThe reaction mixture was treated by the conventional method
  3. distillationthe remained oily material was distilled

Sources & evidence

ORD record
ord-1e6ec2541c2a4eebb85d48e1c7a285e7
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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