Thionyl Chloride → 2-(4-Chlorophenyl)-2-methylpropanoyl chloride

HRID 2110299Notes

Reaction equation

HRID 2110299 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.S(Cl)([Cl:16])=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([Cl:16])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 804062-(4-Chlorophenyl)-2-methylpropionic acid

Product 1

HCID 135368632-(4-Chlorophenyl)-2-methylpropanoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

2-(4-chlorophenyl)-2-methyl propionyl chloride was prepared as follows: To a flask containing 2-(4-chlorophenyl)-2-methyl propionic acid (15.0 g, 75.6 mmol) was added thionyl chloride (approx. 6 mL). Dichloromethane (20 mL) was then added before adding an additional portion of thionyl chloride (approx. 12 mL). The reaction was allowed to heat to 40° C. for two hours before cooling to room temperature and concentrating in vacuo (azeotroping with tetrahydrofuran). The resulting acid chloride was used in the following acylation step without further purification or characterization.

Workup

  1. temperaturebefore cooling to room temperature
  2. concentrationconcentrating in vacuo (azeotroping with tetrahydrofuran)
  3. customThe resulting acid chloride was used in the following acylation step without further purification or characterization

Sources & evidence

ORD record
ord-e575488eaaeb4541af812d7f0cf04527
Source dataset
uspto-grants-2009_04
Patent number
US07517892B2

Reaction notes

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