Thionyl Chloride → 1-Isopropyl-3-oxocyclopentanoyl chloride

HRID 1725759Notes

Reaction equation

HRID 1725759 reaction equation
[CH:1]([C:4]1([C:10]([OH:12])=O)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([CH3:3])[CH3:2].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[CH:1]([C:4]1([C:10]([Cl:15])=[O:12])[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 186143931-Isopropyl-3-oxocyclopentanecarboxylic acid

Product 1

HCID 186143461-Isopropyl-3-oxocyclopentanoyl chlorideYield 30%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 1-isopropyl-3-oxocyclopentylcarboxylic acid (20.1 g, 118.9 mmol) in benzene (150 mL) was slowly treated with thionyl chloride (23.5 mL, 322.1 mmol) and the resulting solution was stirred at 45° C. for 3 hours. The solvent and the volatile components were evaporated under reduced pressure (100 torr) and the residue was distilled to obtain 6.727 g (30%) of the desired product, B.P.: 110-114° C. at 5 torr. 1H NMR (500 MHz, CDCl3): 2.82 (dd, J=18.36, 1.76 Hz, 1H), 2.50 (m, 1H), 2.35 (m, 2H), 2.20 to 190 (bm, 3H), 1.03 (bd, J=8.2 Hz, 6H).

Workup

  1. customThe solvent and the volatile components were evaporated under reduced pressure (100 torr)
  2. distillationthe residue was distilled

Sources & evidence

ORD record
ord-45c9f2e655c046f6960539e3fadef396
Source dataset
uspto-grants-2009_02
Patent number
US07491737B2

Reaction notes

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