Thionyl Chloride → 2,2,5,5-Tetramethylcyclopentanecarbonyl chloride

HRID 231729Notes

Reaction equation

HRID 231729 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[C:9](O)=[O:10].S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:12])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[C:9]([Cl:15])=[O:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10197889Cyclopentanecarboxylic acid, 2,2,5,5-tetramethyl-

Product 1

HCID 139066402,2,5,5-Tetramethylcyclopentanecarbonyl chlorideYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2.51 g of 2,2,5,5-tetramethylcyclopentanecarboxylic acid was dissolved in 10 ml of toluene, and 2.5 ml of thionyl chloride was added thereto. The mixture was stirred at 80° C. for 3 hours. The reaction solution was concentrated and then distilled under reduced pressure, whereby 2.0 g of 2,2,5,5-tetramethylcyclopentanecarbonyl chloride was obtained. Yield 69%. (b.p. 110°-120° C./60 mmHg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-601deb541d284bfda9b0049aeab201e0
Source dataset
uspto-grants-1989_07
Patent number
US04847390

Reaction notes

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