2-Hydroxy-3,4,6-trimethylbenzaldehyde → 2,3,5,6-Tetramethylphenol

HRID 1908874Notes

Reaction equation

HRID 1908874 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[C:8]([CH3:11])[CH:7]=[C:6]([CH3:12])[C:3]=1[CH:4]=O>CO.[C].[Pd]>[CH3:4][C:3]1[C:6]([CH3:12])=[CH:7][C:8]([CH3:11])=[C:9]([CH3:10])[C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 113211462-Hydroxy-3,4,6-trimethylbenzaldehyde

Product 1

HCID 106942,3,5,6-TetramethylphenolYield 12.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

2-Hydroxy-3,4,6-trimethylbenzaldehyde (6.58 g, 40.1 mmol) was dissolved in methanol (120 mL), 10% palladium-carbon (50% water-containing product, 1.0 g) was added under hydrogen atmosphere (balloon pressure), and the mixture was stirred at room temperature for 22 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The precipitated crystals were recrystallized from methanol to give the title compound (0.73 g, yield 12%) as colorless crystals. The mother solution was concentrated under reduced pressure to give second crop (5.10 g, yield 85%). MS m/z 151 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe precipitated crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-3fc14179615c4db1bf7a1c47232f2ae0
Source dataset
uspto-grants-2013_12
Patent number
US08598226B2

Reaction notes

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