Thionyl Chloride → Bis-(cyclohexylmethyl)acetyl chloride

HRID 976052Notes

Reaction equation

HRID 976052 reaction equation
[CH:1]1([CH2:7][CH:8]([CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9](O)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O=S(Cl)[Cl:21]>>[CH:1]1([CH2:7][CH:8]([CH2:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]([Cl:21])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 19968574Bis-(cyclohexylmethyl)acetic acid

Product 1

HCID 19968572Bis-(cyclohexylmethyl)acetyl chlorideYield 92.4%

Procedure

A solution of 2.97 g (11.8 mmol) of bis-(cyclohexylmethyl)acetic acid in 20 mL SOCl2 was stirred at room temperature overnight. The SOCl2 was removed under reduced pressure, the residue taken up in Et2O, and the solvent removed under reduced pressure. The residue was taken up in hexane and the solvent removed under reduced pressure leaving 2.94 g (92.4% yield) of the product as an oil. The structure was confirmed by mass spectroscopy.

Workup

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

Sources & evidence

ORD record
ord-a0abe4882cfd48dc95eeacebf766fe38
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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