Methyl 4'-(benzyloxy)-2',6,6'-trimethylbiphenyl-3-carboxylate → Methyl 4'-hydroxy-2',6,6'-trimethylbiphenyl-3-carboxylate

HRID 508012Notes

Reaction equation

HRID 508012 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=2)=[C:11]([CH3:27])[CH:10]=1)C1C=CC=CC=1>[C].[Pd].C(O)C>[OH:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[CH:17]=2)=[C:11]([CH3:27])[CH:10]=1

Participants

4

Reactant 1

HCID 23157680Methyl 4'-(benzyloxy)-2',6,6'-trimethylbiphenyl-3-carboxylate

Product 1

HCID 23157223Methyl 4'-hydroxy-2',6,6'-trimethylbiphenyl-3-carboxylateYield 103.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of methyl 4′-(benzyloxy)-2′,6,6′-trimethylbiphenyl-3-carboxylate (255 mg, 0.71 mmol), 10% palladium-carbon (50% water-containing product, 25.5 mg) and ethanol (3 mL) was stirred overnight under a hydrogen atmosphere at room temperature. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was again subjected to the above-mentioned conditions (10% palladium-carbon (50% water-containing product, 127 mg), stirring time 2 hr) to give the title compound (199 mg, yield 100%) as a colorless oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. stirringThe residue was again subjected to the above-mentioned conditions (10% palladium-carbon (50% water-containing product, 127 mg), stirring time 2 hr)

Sources & evidence

ORD record
ord-bba42aecde9f4d768d067b27b66dbbdc
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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