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

HRID 1593103Notes

Reaction equation

HRID 1593103 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-4260733f27224af38e7d7a9d14009d5d
Source dataset
uspto-grants-2007_11
Patent number
US07294637B2

Reaction notes

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