Sulfuric Acid → 5-(4-Chlorobenzyl)-2,2-dimethylcyclopentanone

HRID 1699125Notes

Reaction equation

HRID 1699125 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][C:7]2(C#N)[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[C:11](=[O:12])[C:10]([CH3:14])([CH3:13])[CH2:9][CH2:8]2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 112769975-(4-Chlorobenzyl)-5-cyano-2,2-dimethylcyclopentanone

Product 1

HCID 114248965-(4-Chlorobenzyl)-2,2-dimethylcyclopentanoneYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 5-(4-chlorobenzyl)-5-cyano-2,2-dimethylcyclopentanone (5.0 g, 0.02 mole) in water is treated with sulfuric acid (50%, 25 ml), stirred for 5 hours at 140° C., cooled to room temperature, and extracted with toluene. The extracts are combined, washed with water, filtered through celite and concentrated in vacuo to afford the title product as a dark oil, 5.5 g (76.5% pure, 93.1% yield), identified by gas chromatography.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with toluene
  3. washwashed with water
  4. filtrationfiltered through celite and
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8820ce9ba8f463fb0a378a55500a204
Source dataset
uspto-grants-2002_02
Patent number
US06344580B1

Reaction notes

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