Thionyl Chloride → [1-(Chlorocarbonyl)cyclobutyl]methyl acetate

HRID 231607Notes

Reaction equation

HRID 231607 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:8][CH2:9][C:10]1([C:14]([OH:16])=O)[CH2:13][CH2:12][CH2:11]1)(=[O:7])[CH3:6]>>[C:5]([O:8][CH2:9][C:10]1([C:14]([Cl:3])=[O:16])[CH2:13][CH2:12][CH2:11]1)(=[O:7])[CH3:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 156705071-Acetoxymethylcyclobutanecarboxylic Acid

Product 1

HCID 15632048[1-(Chlorocarbonyl)cyclobutyl]methyl acetate

Procedure

Thionyl chloride (1.65 ml, 22.7 mmol) was added to neat 1-acetoxymethylcyclobutanecarboxylic acid (3.3 g, 18.9 mmol). The resulting mixture was stirred at room temperature for 1 hour, then heated on a steam bath for 5 minutes. After cooling, the excess thionyl chloride, HCl and SO2 were removed under reduced pressure (water aspirator). The remained residue was purified by distillation to provide the desired product as a colorless oil: bp 51°-3° C. (0.02 mm); NMR (CDCl3) δ=1.8~2.7 (9H, m containing a singlet at 2.04 δ), 4.40 (2H, s).

Workup

  1. temperatureheated on a steam bath for 5 minutes
  2. temperatureAfter cooling
  3. customthe excess thionyl chloride, HCl and SO2 were removed under reduced pressure (water aspirator)
  4. distillationThe remained residue was purified by distillation

Sources & evidence

ORD record
ord-ec10160d12514ba6a0e8c785090ecde6
Source dataset
uspto-grants-1989_07
Patent number
US04847306

Reaction notes

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