Trifluoroacetic acid → 2-(4-Methylbenzyl)phenol

HRID 1840715Notes

Reaction equation

HRID 1840715 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 2751544Cresyl saligenin

Product 1

HCID 36460202-(4-Methylbenzyl)phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of crude Part A 4-methyl-2′-hydroxybenzhydrol (9.7 g containing no more than 40 mmol) in 175 mL of MeOH was added 0.59 g of 10% Pd/C and 1.75 mL of TFA. The suspension was stirred for 40 hr under 1 atmos. H2, filtered through celite and concentrated to yield 8.6 of crude 2-(4′-methylbenzyl)phenol as an oil.

Workup

  1. filtrationH2, filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-e2df7b3e911e4dd7a086b3f53bef24c9
Source dataset
uspto-grants-2004_01
Patent number
US06683056B2

Reaction notes

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