Acetyl chloride → 2-Methylene-4-ethoxycarbonylbutyric acid

HRID 65789Notes

Reaction equation

HRID 65789 reaction equation
[CH2:1]=[C:2]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])[C:3]([OH:5])=[O:4].[C:11](Cl)(=O)[CH3:12]>>[CH2:1]=[C:2]([CH2:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([OH:5])=[O:4]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 951552-Methyleneglutaric acid

Product 1

HCID 197450382-Methylene-4-ethoxycarbonylbutyric acid

Procedure

A mixture of 2-methyleneglutaric acid [Ber. 34, 427 (1901)] (40 g.) and acetyl chloride (80 ml.) is heated on the steam bath for 1.5 hours. The excess acetyl chloride is removed in vacuo (75°) and the residue is evaporated from toluene twice. Finally, the residue is dissolved in ethanol and heated on the steam bath for one hour. The reaction mixture is concentrated to dryness to yield 2-methylene-4-(ethoxycarbonyl)butyric acid.

Workup

  1. temperatureis heated on the steam bath for 1.5 hours
  2. customThe excess acetyl chloride is removed in vacuo (75°)
  3. customthe residue is evaporated from toluene twice
  4. dissolutionFinally, the residue is dissolved in ethanol
  5. temperatureheated on the steam bath for one hour
  6. concentrationThe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-4287e6c765554180ae49536cb7ed3995
Source dataset
uspto-grants-1978_12
Patent number
US04128721

Reaction notes

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