Dimethylformamide → 2-Phenylbutyryl chloride

HRID 249537

Reaction equation

HRID 249537 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH:11]([CH2:15][CH3:16])[C:12](O)=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CN(C=O)C>C(Cl)Cl>[C:5]1([CH:11]([CH2:15][CH3:16])[C:12]([Cl:3])=[O:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70122-Phenylbutyric AcidHCID 24386Thionyl Chloride

Product 1

HCID 981732-Phenylbutyryl chlorideYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.12 mol) in 60 mL of CH2Cl2 was added to a stirred solution of 2-phenylbutyric acid (16.4 g, 0.10 mol). A catalytic amount of DMF was added and the reaction was allowed to continue overnight at room temperature. The volatiles were removed under vacuum and the residual liquid was vacuum distilled to yield 12.4 g (68%) of 2-phenylbutyryl chloride. IR (neat) 1798 cm-1 (C=O).

Workup

  1. customThe volatiles were removed under vacuum
  2. distillationdistilled

Sources & evidence

ORD record
ord-27d8209bcb5d425b9dd1ab8a3f96bc9c
Source dataset
uspto-grants-1993_05
Patent number
US05214191

Linked notes

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