Thionyl Chloride → 4-Chlorobenzenepropanoyl chloride

HRID 1795180Notes

Reaction equation

HRID 1795180 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([Cl:15])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 123137beta-(p-Chlorophenyl)propionic acid

Product 1

HCID 122065164-Chlorobenzenepropanoyl chlorideYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-(4-chloro-phenyl)-propionic acid (1.5 g, 8.15 mmol) in benzene (50 mL) is added thionyl chloride (1.18 mL, 16.3 mmol). The resulting solution is heated to reflux for twenty-four hours and then cooled to room temperature. The solvents are removed under reduced pressure to afford 1.45 g (88% yield) of the desired compound as a colorless oil. The crude product is used without further purification. 1H NMR (CDCl3 300 MHz) δ 3.01 (t, J=7.2 Hz, 2H), 3.22 (t, J=6.9 Hz, 2H), 7.12–7.20 (m, 2H), 7.26–7.35 (m, 2H).

Workup

  1. temperatureThe resulting solution is heated
  2. temperatureto reflux for twenty-four hours
  3. customThe solvents are removed under reduced pressure

Sources & evidence

ORD record
ord-0685a249b92642f7b123a8ff739bc3e7
Source dataset
uspto-grants-2006_04
Patent number
US07026335B2

Reaction notes

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