Acetyl chloride → 2-Methylene-4-ethoxycarbonylbutyric acid

HRID 262374Notes

Reaction equation

HRID 262374 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 chlorine (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-b53193bb804d428a8b38e04b71de9a13
Source dataset
uspto-grants-1979_05
Patent number
US04154736

Reaction notes

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