Methanol → 3-[(Benzyloxy)methyl]cyclohexanone

HRID 1956749Notes

Reaction equation

HRID 1956749 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH:12]([OH:16])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CO>CC(C)=O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 157273243-BenzyloxymethylcyclohexanolHCID 131709961Jones' reagent

Product 1

HCID 138462513-[(Benzyloxy)methyl]cyclohexanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of the compound (10) (4.9 g; 22.2 mmol) in acetone (90 ml), Jones reagent (chromic anhydride acid-sulfuric acid) (0.07 mol) is dropwise added, and the resultant mixture is stirred at a temperature of 0° to 10° C. for 2 hours. Methanol is dropwise added to the reaction mixture, which is poured into ice-water and extracted with chloroform. The extract is washed with water, dried and concentrated under reduced pressure. The residue is chromatographed on a silica gel column to give 3-benzyloxymethylcyclohexanone (11).

Workup

  1. extractionextracted with chloroform
  2. washThe extract is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is chromatographed on a silica gel column

Sources & evidence

ORD record
ord-be572945661d407cafdcb44780407515
Source dataset
uspto-grants-1998_07
Patent number
US05780632

Reaction notes

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