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

HRID 1520857Notes

Reaction equation

HRID 1520857 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, 1H) 2.27-2.15 (m, 2H) 2.14-2.06 (m, 2H) 1.18 (s, 3H) 1.12 (s, 3H).

Workup

  1. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-9d4476b202944afda5bada1eaa679d36
Source dataset
uspto-grants-2015_07
Patent number
US09073871B2

Reaction notes

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