Acetyl chloride → 2-Methylene-4-ethoxycarbonylbutyric acid

HRID 2049785Notes

Reaction equation

HRID 2049785 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-2dd0e1c0b3d04f53a969b5e3eb683208
Source dataset
uspto-grants-1980_04
Patent number
US04198517

Reaction notes

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