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

HRID 2042183Notes

Reaction equation

HRID 2042183 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>C(Cl)Cl.CN(C=O)C>[Cl:15][C:7]([C:6]([CH3:11])([CH3:10])[CH2:5][O:4][C:1](=[O:3])[CH3:2])=[O:8]

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 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of acetoxy-2,2-dimethyl-propionic acid (example 40, step 1) (2.2 g, 13.75 mmol) in CH2Cl2 (25 ml), were added oxalyl chloride (2.62 ml, 27.50 mmol) and 2-4 drops of DMF and stirred at 25° C. for 3 hours. The solvent was evaporated and the resulting acetic acid 2-chlorocarbonyl-2-methyl-propyl ester (2.4 g) was used directly in next step without purification.

Workup

  1. customThe solvent was evaporated
  2. customthe resulting acetic acid 2-chlorocarbonyl-2-methyl-propyl ester (2.4 g) was used directly in next step without purification

Sources & evidence

ORD record
ord-47d8682c2d9b41748a5777f1be30610b
Source dataset
uspto-grants-2013_11
Patent number
US08586581B2

Reaction notes

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