Thionyl Chloride → 3-(2-Biphenylyl)-2-ethylpropionyl chloride

HRID 1256

Reaction equation

HRID 1256 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH:8]([CH2:12][CH3:13])[C:9](O)=[O:10].S(Cl)([Cl:22])=O>>[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH:8]([CH2:12][CH3:13])[C:9]([Cl:22])=[O:10]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 215719833-(2-Biphenylyl)-2-ethylpropionic acid

Product 1

HCID 223402173-(2-Biphenylyl)-2-ethylpropionyl chlorideYield 106.3%

Procedure

A 100-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a thermometer and a NaOH trap was charged with 13.3 g (52.4 mmol) of 3-(2-biphenylyl)-2-ethylpropionic acid and 25.9 ml (355 mmol) of thionyl chloride, and the resulting mixture was stirred under reflux for 2.5 hours under a nitrogen atmosphere. After the reaction was completed, the unreacted thionyl chloride was distilled off under reduced pressure to obtain 15.2 g of a crude product as a yellow-orange liquid. The thus obtained acid chloride was used in the next reaction without further purification.

Workup

  1. customA 100-ml three-necked round flask equipped with a stirring bar
  2. temperatureunder reflux for 2.5 hours under a nitrogen atmosphere
  3. distillationthe unreacted thionyl chloride was distilled off under reduced pressure

Sources & evidence

ORD record
ord-54b03352f0df47deb65aac6e35fc4ae0
Source dataset
uspto-grants-1998_03
Patent number
US05723640

Linked notes

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