Oxalyl chloride → 2,2-Dimethyl-3-acetyloxypropionyl chloride

HRID 1995491Notes

Reaction equation

HRID 1995491 reaction equation
[C:1]([O:4][CH2:5][C:6]([CH3:11])([CH3:10])[C:7](O)=[O:8])(=[O:3])[CH3:2].C(Cl)(=O)C([Cl:15])=O>C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]([CH3:11])([CH3:10])[C:7]([Cl:15])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 131926213-(Acetyloxy)-2,2-dimethylpropanoic acid

Product 1

HCID 111946632,2-Dimethyl-3-acetyloxypropionyl chlorideYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Under an argon atmosphere a stirred solution of 1.2 grams (0.008 mole) of 3-acetoxy-2,2-dimethylpropionic acid in 30 ml of toluene was heated to 80° and a solution of 1.9 grams (0.015 mole) of oxalyl chloride in 20 ml of toluene was added dropwise. Upon completion of addition the reaction mixture was heated at 80° for 18 hours. The reaction mixture was concentrated under reduced pressure to give 1.3 grams of 3-acetoxy-2,2-dimethylpropionyl chloride as an oil.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperaturewas heated at 80° for 18 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2b65daf34e0746008758c8009fa7375b
Source dataset
uspto-grants-1983_09
Patent number
US04405357

Reaction notes

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