Dichloromethane → HCID 23443014, compound

HRID 366770Notes

Reaction equation

HRID 366770 reaction equation
[OH:1][C:2]([CH:5]1[CH2:9][CH2:8][CH:7]([CH3:10])[CH:6]1[OH:11])([CH3:4])[CH3:3].ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(OCC)C>[OH:1][C:2]([CH:5]1[CH2:9][CH2:8][CH:7]([CH3:10])[C:6]1=[O:11])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 23443037HCID 23443037, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 23443014HCID 23443014, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7.9 g of 2-(1-hydroxyisopropyl)-5-methyl-cyclopentanol was added dropwise to 100 ml of a dichloromethane suspension containing 16.2 g pyridinium chlorochromate and the mixture was stirred for 5 hours at room temperature. The reaction solution was admixed with diethylether and stirred. Then, the chromate was filtered out and the filtrate was condensed under a vacuum. The residue was purified by means of silica gel column chromatography (eluent: hexane/ethylacetate=7/3) and 6.6 g of 2-(1-hydroxyisopropyl)-5-methyl-cyclopentanone was obtained as an oily substance (yield: 86%).

Workup

  1. stirringstirred
  2. filtrationThen, the chromate was filtered out
  3. customcondensed under a vacuum
  4. customThe residue was purified by means of silica gel column chromatography (eluent: hexane/ethylacetate=7/3)

Sources & evidence

ORD record
ord-d876bf889ff849d88209c975629952ae
Source dataset
uspto-grants-2000_10
Patent number
US06130255

Reaction notes

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