Acetyl chloride → 2-Methylene-4-ethoxycarbonylbutyric acid

HRID 372382Notes

Reaction equation

HRID 372382 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 1 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 1 hour
  6. concentrationThe reaction mixture is concentrated to dryness

Sources & evidence

ORD record
ord-a5365f2d96e646a9a884dfed8a873a55
Source dataset
uspto-grants-1978_05
Patent number
US04091024

Reaction notes

Loading…