Oxalyl chloride → 2,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

HRID 538802Notes

Reaction equation

HRID 538802 reaction equation
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7](O)=[O:8].C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl.CN(C)C=O>[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([Cl:14])=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acid

Product 1

HCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideYield 99.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,3,3-tetramethylcyclopropanecarboxylic acid (0.50 g, 3.5 mmol) in 18 mL of methylene chloride at 0° C. was added oxalyl chloride (0.61 mL, 7.0 mmol) and a catalytic amount of dimethylformamide (2 drops). The solution was stirred at ambient temperature for 1 hour, and then concentrated under reduced pressure to provide 0.56 g of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2742096f492248e396f370286cf55668
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

Loading…