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

HRID 1424253Notes

Reaction equation

HRID 1424253 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) 2.15-2.27 (m, 2H) 2.06-2.14 (m, 2H) 1.18 (s, 3H) 1.12 (s, 3H).

Workup

  1. concentrationbefore concentrating in vacuo

Sources & evidence

ORD record
ord-f0dcdbbc3ee047e69f8ffca6d2dae1ed
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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