Thionyl Chloride → (Dibenzyl)acetyl chloride

HRID 976044Notes

Reaction equation

HRID 976044 reaction equation
[CH2:1]([CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:21]>>[CH2:1]([CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:9]([Cl:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 64800Benzenepropanoic acid, alpha-(phenylmethyl)-

Product 1

HCID 12394381(Dibenzyl)acetyl chlorideYield 94.1%

Procedure

To 20 mL of SOCl2 was added in portions 3.14 g (13.1 mmol) of di-benzylacetic acid and the solution stirred at room temperature overnight. The SOCl2 was removed under reduced pressure and the residue taken up in Et2O and the solvent removed again. There was obtained 3.18 g (94.1% yield) of the product as an oil. The structure was confirmed by NMR spectroscopy.

Workup

  1. customThe SOCl2 was removed under reduced pressure
  2. customthe solvent removed again

Sources & evidence

ORD record
ord-ab89ef045e2e4027a423d7a5c5ba4430
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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