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

HRID 1954852Notes

Reaction equation

HRID 1954852 reaction equation
[F: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>>[F: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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 1363023-(4-Fluorophenyl)propionic acid

Product 1

HCID 219642583-(4-Fluorophenyl)propionyl chlorideYield 96.3%

Procedure

A mixture of 3-(4-fluorophenyl)propionic acid (275.1 g, 1.6 mol) and thionyl chloride (300 mL, 4.1 mol) was heated to reflux for 3 h, cooled to room temperature and distilled under aspirator vacuum to give 287.6 g (96%) of 3-(4-fluorophenyl)propionyl chloride as a pale pink oil, b.p., 120-122° C./15 mm Hg;

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. distillationdistilled under aspirator vacuum

Sources & evidence

ORD record
ord-99ea643a165f44458e75d1d652af2e01
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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