Thionyl Chloride → 2-(4-Methoxyphenyl)propanoyl chloride

HRID 1522688Notes

Reaction equation

HRID 1522688 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10](O)=[O:11])=[CH:5][CH:4]=1.S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])[C:10]([Cl:16])=[O:11])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 257576p-Methoxyphenylpropionic acid

Product 1

HCID 149460772-(4-Methoxyphenyl)propanoyl chloride

Procedure

Under an argon atmosphere, 2-(4-methoxyphenyl)propanoic acid (synthesized by the process of I. Shiina, et al., Eur J. Org. Chem., 5887-5890 (2008)) (1.20 g, 6.66 mmol) was dissolved in thionyl chloride (6.00 mL, 82.6 mmol) and the solution was heated to reflux for 27 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure to give the crude product of 2-(4-methoxyphenyl)propanoyl chloride (16) as a colorless oil. The product was used in the following reaction without further purification.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 27 hours
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a76b08180bc04ad081067c4c76c1a551
Source dataset
uspto-grants-2015_07
Patent number
US09075058B2

Reaction notes

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