Cyclohexaneacetic acid → Cyclohexylacetyl chloride

HRID 1883478Notes

Reaction equation

HRID 1883478 reaction equation
[CH:1]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:13])=O>>[CH:1]1([CH2:7][C:8]([Cl:13])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21363Cyclohexaneacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 2757989Cyclohexylacetyl chlorideYield 77%

Conditions

Temperature
50 °C

Procedure

Cyclohexyl-acetic acid (288 ml, 2.04 mol) and thionyl chloride (306 ml, 4.19 mol) were stirred in a 1000 ml flask fitted with reflux condenser, CaCl2 drying tube, thermometer, heating mantle, and magnetic stirrer. The reaction solution was heated to 50° C. with stirring (gas evolution). After 14.5 hours at 50° C., the reaction mixture was further heated to a gentle reflux for 90 min and then cooled to room temperature. Excess thionyl chloride was removed under reduced pressure. The residual liquid was vacuum distilled to afford cyclohexyl-acetyl chloride (250.92 g, 77%) as a pale yellow liquid. bp.: 60° c./5 mm Hg; MS m/z: 161 (M+H)+.

Workup

  1. customfitted
  2. temperaturewith reflux condenser, CaCl2 drying tube
  3. temperaturethermometer, heating mantle
  4. temperaturethe reaction mixture was further heated to
  5. temperaturea gentle reflux for 90 min
  6. temperaturecooled to room temperature
  7. customExcess thionyl chloride was removed under reduced pressure
  8. distillationdistilled

Sources & evidence

ORD record
ord-8c69eb8752414d72a380d4446a8e9fcd
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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