(2-(Benzyloxy)biphenyl-3-yl)(2-methoxybiphenyl-3-yl)methanol → (2-(Benzyloxy)biphenyl-3-yl)(2-methoxybiphenyl-3-yl)methanone

HRID 1042511Notes

Reaction equation

HRID 1042511 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]([C:17]2[C:18]([O:29][CH3:30])=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=[CH:21][CH:22]=2)[OH:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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[C:14]([C:15]([C:17]2[C:18]([O:29][CH3:30])=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:20]=[CH:21][CH:22]=2)=[O:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58238521(2-(Benzyloxy)biphenyl-3-yl)(2-methoxybiphenyl-3-yl)methanol

Product 1

HCID 58238522(2-(Benzyloxy)biphenyl-3-yl)(2-methoxybiphenyl-3-yl)methanoneYield 62%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of crude 3 (3.46 mmol) in dichloromethane (60 mL) was treated with manganese dioxide (85%, 5.3 g, 15 equiv) and this suspension was stirred at reflux overnight. The solids were filtered out and washed with ethyl acetate. The solvent was removed in a rotary evaporator and the residue was chromatographed on silica (85 g) with 2% ethyl acetate in heptane (5 L). Pure 4 (0.48 g) as well as slightly impure 4 (1.01 g) were isolated (total yield 91%).

Workup

  1. temperatureat reflux overnight
  2. filtrationThe solids were filtered out
  3. washwashed with ethyl acetate
  4. customThe solvent was removed in a rotary evaporator
  5. customthe residue was chromatographed on silica (85 g) with 2% ethyl acetate in heptane (5 L)

Sources & evidence

ORD record
ord-9d78099182e24def88e3ccc4d7b0ae5d
Source dataset
uspto-grants-2013_10
Patent number
US08557936B2

Reaction notes

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