2-(3-Methoxyphenyl)-cyclopentanol → 2-(3-Methoxyphenyl)cyclopentan-1-one

HRID 418900

Reaction equation

HRID 418900 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[OH:14])[CH:6]=[CH:7][CH:8]=1.[Cr](Cl)(O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 27596482-(3-Methoxyphenyl)-cyclopentanolHCID 178526118HCID 178526118, compound

Product 1

HCID 123629382-(3-Methoxyphenyl)cyclopentan-1-oneYield 69,131.797%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)-cyclopentanol (6.4 g, 0.033 mmoles) in 140 ml of methylene chloride, add a mixture of pyridine chlorochromate (14.4 g, 0.066 mmoles), and silica gel (14.4 g). After 1.5 hours, an equivalent amount of oxidizing agent and silica gel is added and the reaction is stirred an additional 3.5 hours. Reduce the solvent in half in vacuo at 35° C. and chromatograph on silica with 3-1 hexanes-ethyl acetate to yield 4.34 g of the titled compound. 1H NMR (CDCl3): 7.25 (m, 1H), 6.81-6.74 (m, 3H), 3.8 (s, 3H), 3.31 (m, 1H), 2.5 (m, 2H), 2.3 (m, 1H), 2.1 (m, 2H), 1.9 (m, 1H).

Workup

  1. additionis added

Sources & evidence

ORD record
ord-738078e0ef6a4d98ad540e558f77b71f
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Linked notes

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