Acetyl chloride → 3-(Acetyloxy)-2,2-dimethylpropanoic acid

HRID 1426233Notes

Reaction equation

HRID 1426233 reaction equation
[OH:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].[C:9](Cl)(=[O:11])[CH3:10]>>[C:9]([O:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5])(=[O:11])[CH3:10]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 785483-Hydroxy-2,2-dimethylpropionic acid

Product 1

HCID 131926213-(Acetyloxy)-2,2-dimethylpropanoic acidYield 81%

Procedure

A solution of 3-hydroxy-2,2-dimethyl-propionic acid (1.5 g, 12.69 mmol) in 5 ml of acetyl chloride was heated at 80° C. under nitrogen for 2 hours. The excess of acetyl chloride was evaporated under reduced pressure. The resulting residue was dissolved in dichloromethane and washed with water. The organic layer was separated, dried and evaporated to get the desired 3-acetoxy-2,2-dimethyl-propionic acid (1.65 g, 81% yield) as a colorless liquid.

Workup

  1. customThe excess of acetyl chloride was evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe organic layer was separated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-758a3fe2d8d147c4a86fed037bd2fe5b
Source dataset
uspto-grants-2015_01
Patent number
US08933094B2

Reaction notes

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