Thionyl Chloride → 3-(4-Methoxyphenyl)propionyl chloride

HRID 993050Notes

Reaction equation

HRID 993050 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([Cl:16])=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 957503-(p-Methoxyphenyl)propionic acid

Product 1

HCID 109324413-(4-Methoxyphenyl)propionyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 3-(4-Methoxyphenyl)propionic acid (10 g) in 150 ml of toluene are added 8 ml of thionyl chloride and the mixture is heated to 65° C. for 4 hours. The solvent is evaporated off under reduced pressure and the residue is redissolved in toluene and concentrated to dryness. Such steo is repeated twice. 11 g of the product are obtained as a yellow oil.

Workup

  1. customThe solvent is evaporated off under reduced pressure
  2. dissolutionthe residue is redissolved in toluene
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-40fd248ea35049fdbad7ae1df8c27c33
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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