(2-Cyclopropyl-4'-fluoro-6-propoxybiphenyl-4-yl)methanol → 2-Cyclopropyl-4'-fluoro-6-propoxybiphenyl-4-carbaldehyde

HRID 531012Notes

Reaction equation

HRID 531012 reaction equation
[CH:1]1([C:4]2[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[C:6]([O:12][CH2:13][CH2:14][CH3:15])[C:5]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:3][CH2:2]1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[CH:1]1([C:4]2[CH:9]=[C:8]([CH:10]=[O:11])[CH:7]=[C:6]([O:12][CH2:13][CH2:14][CH3:15])[C:5]=2[C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 117992501(2-Cyclopropyl-4'-fluoro-6-propoxybiphenyl-4-yl)methanol

Product 1

HCID 904235562-Cyclopropyl-4'-fluoro-6-propoxybiphenyl-4-carbaldehydeYield 74.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

Manganese dioxide (60.4 g) was added to a mixture of (2-cyclopropyl-4′-fluoro-6-propoxybiphenyl-4-yl)methanol (29.8 g) and toluene (200 mL), and the resultant mixture was stirred at 60° C. for 1 hour in a nitrogen atmosphere. The reaction mixture was filtered, and then, the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (22.1 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-656125c671a94b01878d964f481d6b9f
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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