1-[5-(Benzyloxy)-2-nitrophenyl]-3-methyl-2-buten-1-ol → 1-[5-(Benzyloxy)-2-nitrophenyl]-3-methyl-2-buten-1-one

HRID 396127Notes

Reaction equation

HRID 396127 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:21]([O-:23])=[O:22])=[C:13]([CH:15]([OH:20])[CH:16]=[C:17]([CH3:19])[CH3:18])[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+:21]([O-:23])=[O:22])=[C:13]([C:15](=[O:20])[CH:16]=[C:17]([CH3:19])[CH3:18])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 230030561-[5-(Benzyloxy)-2-nitrophenyl]-3-methyl-2-buten-1-ol

Product 1

HCID 230030801-[5-(Benzyloxy)-2-nitrophenyl]-3-methyl-2-buten-1-oneYield 81%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

In an analogous manner to the procedure of Example VI, 1.70 g (5.43 mmol) of 1-[5-(benzyloxy)-2-nitrophenyl]-3-methyl-2-buten-1-ol are reacted with 4.25 g (48.83 mmol) of manganese dioxide in 30 ml of dichloromethane to give 1.37 g (81%) of 1-[5-(benzyloxy)-2-nitrophenyl]-3-methyl-2-buten-1-one.

Sources & evidence

ORD record
ord-ca38cbf5acbd48478ae5daaecad29d56
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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