Thionyl Chloride → 2-(4-ethoxyphenyl)acetyl Chloride

HRID 1796452

Reaction equation

HRID 1796452 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)[CH3:2].S(Cl)([Cl:16])=O>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([Cl:16])=[O:13])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 78631Benzeneacetic acid, 4-ethoxy-

Product 1

HCID 116297822-(4-ethoxyphenyl)acetyl ChlorideYield 94.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (4-ethoxyphenyl)acetic acid (10.0 g, 55.5 mmol) in benzene (100 mL) was added thionyl chloride (50 mL, 68.5 mmol) and the reaction mixture was stirred at 80° C. for 2 hours. The solvent was evaporated in vacuo and the crude product was purified by distillation (bp 86° C., 0.4 Torr) to provide the title compound (10.39 g, 94%) as a yellow oil. MS of methyl ester: MS (ESI) (M+H)+=194.

Workup

  1. customThe solvent was evaporated in vacuo
  2. distillationthe crude product was purified by distillation (bp 86° C., 0.4 Torr)

Sources & evidence

ORD record
ord-a4973ff8d05341179cbddab8e5d61986
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Linked notes

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