Oxalyl chloride → 3,3-Dimethylcyclobutane-1-carbonyl chloride

HRID 537460

Reaction equation

HRID 537460 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:5][CH:4]([C:6](O)=[O:7])[CH2:3]1.C(Cl)(=O)C([Cl:13])=O>ClCCl.CN(C)C=O>[CH3:1][C:2]1([CH3:9])[CH2:5][CH:4]([C:6]([Cl:13])=[O:7])[CH2:3]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 2151063,3-Dimethylcyclobutanecarboxylic acid

Product 1

HCID 205352373,3-Dimethylcyclobutane-1-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 3,3-dimethylcyclobutanecarboxylic acid (1.35 g, 10.5 mmol) in dichloromethane (10 mL) was slowly added oxalyl chloride (4.01 g, 31.6 mmol) and 1 drop of N,N-dimethylformamide. The reaction was warmed to room temperature and stirred for 2 hours. The reaction was concentrated in vacuo to give crude 3,3-dimethylcyclobutanecarbonylchloride (1.54 g) as a yellow oil.

Workup

  1. customTo a 0° C.
  2. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-f6fe8d442e40482e9aa1047922ee3ebe
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Linked notes

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