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

HRID 232117Notes

Reaction equation

HRID 232117 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>CN(C=O)C.C1C=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

5

Reactant 2

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

Product 1

HCID 111946632,2-Dimethyl-3-acetyloxypropionyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A benzene solution (25 ml) of crude 3-acetoxy-2,2-dimethyl proprionic acid from Example 3(a) (7.4 g, 46.5 mmol), oxalyl chloride (6.45 g, 51 ml) and DMF (2 drops) was stirred at ambient temperature for 3 hours. The pale yellow solution was distilled to provide the title compound as a colorless liquid, b.p.15 85°-88° C. NMR (CDCl3) δ 4.18 (2 H, s), 2.08 (3 H, s), 1.35 (6 H, s).

Workup

  1. distillationThe pale yellow solution was distilled

Sources & evidence

ORD record
ord-9f041b6e50de4083a1058d9df9db30ee
Source dataset
uspto-grants-1989_07
Patent number
US04851436

Reaction notes

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