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

HRID 2042182Notes

Reaction equation

HRID 2042182 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-a092a93446a44a4c96ad09c933334e0f
Source dataset
uspto-grants-2013_11
Patent number
US08586581B2

Reaction notes

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