1-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol → 1-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-one

HRID 396126Notes

Reaction equation

HRID 396126 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:20]([O-:22])=[O:21])=[C:13]([CH:15]([OH:19])[C:16]([CH3:18])=[CH2:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:20]([O-:22])=[O:21])=[C:13]([C:15](=[O:19])[C:16]([CH3:18])=[CH2:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 230030651-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol

Product 1

HCID 230030601-[5-(Benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-oneYield 85.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3.67 g (42.23 mmol) of manganese dioxide are suspended in a solution of 1.58 g (5.28 mmol) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-ol in 30 ml of dichloromethane. The suspension is heated under reflux overnight, and after cooling to room temperature the mixture is filtered through kieselguhr, the residue is washed with dichloromethane and the filtrate is concentrated in vacuo and dried. 1.34 g (85%) of 1-[5-(benzyloxy)-2-nitrophenyl]-2-methyl-2-propen-1-one are obtained.

Workup

  1. temperatureThe suspension is heated
  2. temperatureunder reflux overnight
  3. filtrationis filtered through kieselguhr
  4. washthe residue is washed with dichloromethane
  5. concentrationthe filtrate is concentrated in vacuo
  6. customdried

Sources & evidence

ORD record
ord-0cba0ba3da9f4e8a81f9a388e6936256
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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