Thionyl Chloride → Cyclopentylacetyl chloride

HRID 1730665Notes

Reaction equation

HRID 1730665 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:12])=O>CN(C)C=O>[CH:1]1([CH2:6][C:7]([Cl:12])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 71606Cyclopentylacetic acid

Product 1

HCID 3485182Cyclopentylacetyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 50 g. of cyclopentaneacetic acid containing 2.9 ml. of N,N-dimethylformamide is added dropwise with stirring, 51 g. of thionyl chloride over a period of 15 minutes. After stirring for an additional 60 minutes excess thionyl chloride is removed in vacuo and the residual oil is distilled to give 55.4 g. (97%) of product, b.p. 57°-58° C. (10 mm.).

Workup

  1. customis removed in vacuo
  2. distillationthe residual oil is distilled
  3. customto give 55.4 g

Sources & evidence

ORD record
ord-7e37dd16e47f4775b6c453b0098b0049
Source dataset
uspto-grants-1976_11
Patent number
US03993674

Reaction notes

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