HCID 58439122, compound → HCID 58439097, compound

HRID 217452Notes

Reaction equation

HRID 217452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH2:23][OH:24])=[C:20]([OH:22])[CH:21]=2)=[CH:10][C:9]=1[C:25]([F:28])([F:27])[F:26]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH:23]=[O:24])=[C:20]([OH:22])[CH:21]=2)=[CH:10][C:9]=1[C:25]([F:26])([F:27])[F:28]

Participants

4

Reactant 1

HCID 58439122HCID 58439122, compound

Product 1

HCID 58439097HCID 58439097, compoundYield 34.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 5-({[2′-fluoro-2-(trifluoromethyl)biphenyl-4-yl]oxy}methyl)-2-(hydroxymethyl)phenol (520 mg) in chloroform (10 mL) was added manganese dioxide (1 g) at room temperature. The reaction liquid was stirred at room temperature for 16 hours, and then filtered through celite. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (hexane:EtOAc=95:5 to 80:20) to obtain 4-({[2′-fluoro-2-(trifluoromethyl)biphenyl-4-yl]oxy}methyl)-2-hydroxybenzaldehyde (180 mg) as a white solid.

Workup

  1. customThe reaction liquid
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (hexane:EtOAc=95:5 to 80:20)

Sources & evidence

ORD record
ord-dec8629f4ee34175967224836d38cf39
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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