Thionyl Chloride → 3-Cyclopentyl-2-phenylpropionyl chloride

HRID 889600Notes

Reaction equation

HRID 889600 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:19])=O>CN(C=O)C>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([Cl:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 186266423-Cyclopentyl-2-phenylpropanoic acid

Product 1

HCID 866254663-Cyclopentyl-2-phenylpropionyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

To the title B compound, 3-cyclopentyl-2-phenylpropionic acid (3.1 g, 14.2 mmol) is added 10 mL of thionyl chloride and one drop of DMF. The reaction mixture is stirred at ambient temperature for 2 h. The excess thionyl chloride is evaporated and the residue is twice treated with toluene and evaporated to yield 3-cyclopentyl-2-phenylpropionyl chloride as an orange-yellow oil which is selected as such without further purification.

Workup

  1. customThe excess thionyl chloride is evaporated
  2. additionthe residue is twice treated with toluene
  3. customevaporated

Sources & evidence

ORD record
ord-6b5f13eb86734be696b006115b1e12de
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

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