(4'-(Benzyloxy)-2,2',6'-trimethylbiphenyl-3-yl)methanol → 3'-(Hydroxymethyl)-2,2',6-trimethylbiphenyl-4-ol

HRID 2280656Notes

Reaction equation

HRID 2280656 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][OH:23])[C:17]=2[CH3:24])=[C:11]([CH3:25])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[OH:23][CH2:22][C:18]1[C:17]([CH3:24])=[C:16]([C:12]2[C:11]([CH3:25])=[CH:10][C:9]([OH:8])=[CH:14][C:13]=2[CH3:15])[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 89701782(4'-(Benzyloxy)-2,2',6'-trimethylbiphenyl-3-yl)methanol

Product 1

HCID 683329993'-(Hydroxymethyl)-2,2',6-trimethylbiphenyl-4-olYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(4′-(Benzyloxy)-2,2′,6′-trimethylbiphenyl-3-yl)methanol 12c (190 mg, 0.57 mmol) was dissolved in 5 mL of methanol, followed by addition of Pd/C (20 mg, 10%) under hydrogen atomosphere. The reaction solution was stirred for 12 hours. The resulting solution was filtered, and the filtrate was concentrated under reduced pressure to obtain the crude title compound 3′-(hydroxymethyl)-2,2′,6-trimethylbiphenyl-4-ol 12d (128 mg) as a yellow solid, which was used directly in the next step without further purification.

Workup

  1. filtrationThe resulting solution was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-844baf1510b544ce904b4cae442b56e6
Source dataset
uspto-grants-2015_09
Patent number
US09139548B2

Reaction notes

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