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

HRID 2281124Notes

Reaction equation

HRID 2281124 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>[CH3:1][C:2]1([CH3:9])[CH2:5][CH:4]([C:6]([Cl:13])=[O:7])[CH2:3]1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 2151063,3-Dimethylcyclobutanecarboxylic acid

Product 1

HCID 205352373,3-Dimethylcyclobutane-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,3-Dimethyl-cyclobutanecarboxylic acid (Parkway Scientific, New York, N.Y., USA) (500 mg, 3.90 mmol) was dissolved in dichloromethane (3 mL) and oxalyl chloride (1.02 mL, 11.7 mmol) was added. The solution was stirred at room temperature for 4 h before concentrating in vacuo to provide 3,3-dimethylcyclobutanecarbonyl chloride which was carried on without purification. 1H NMR (400 MHz, CDCl3) δ 3.49 (quin, J=8.9 Hz, 1 H) 2.15-2.27 (m, 2 H) 2.06-2.14 (m, 2 H) 1.18 (s, 3 H) 1.12 (s, 3 H).

Workup

  1. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-30564473682c47f98b711c669090cb82
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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