Thionyl Chloride → 3-(3,4-Dimethylphenyl)propanoyl chloride

HRID 1017137Notes

Reaction equation

HRID 1017137 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([OH:13])=O)[CH:5]=[CH:6][C:7]=1[CH3:8].S(Cl)([Cl:16])=O>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][C:11]([Cl:16])=[O:13])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 38702183-(3,4-dimethylphenyl)propanoic Acid

Product 1

HCID 184028493-(3,4-Dimethylphenyl)propanoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1 L three-neck round bottom flask equipped with a condenser, magnetic stir bar, thermometer, and a nitrogen inlet was charged with 3-(3,4-dimethylphenyl) propionic acid (64.0 g, 0.359 mol), dichloromethane (500 mL), and thionyl chloride (110 mL, 1.5 mol). The reaction mixture was stirred at reflux for 7 hours. Dichloromethane and excess thionyl chloride were removed by rotary evaporation under reduced pressure to yield 3-(3,4-dimethylphenyl)propionyl chloride as an amber oil (70.6 g, 100% conversion by GC).

Workup

  1. customA 1 L three-neck round bottom flask equipped with a condenser, magnetic stir bar
  2. temperatureat reflux for 7 hours
  3. customDichloromethane and excess thionyl chloride were removed by rotary evaporation under reduced pressure

Sources & evidence

ORD record
ord-06f6f6fb885b4eb5a01d46efb3f6f4b0
Source dataset
uspto-grants-2002_11
Patent number
US06479424B1

Reaction notes

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