2-Benzyloxy-4,5-dimethoxybenzaldehyde → 2-Hydroxy-4,5-dimethoxybenzaldehyde

HRID 252850Notes

Reaction equation

HRID 252850 reaction equation
C([O:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:10]=1[CH:11]=[O:12])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:10]=1[CH:11]=[O:12]

Participants

4

Reactant 1

HCID 5637842-Benzyloxy-4,5-dimethoxybenzaldehyde

Product 1

HCID 109869082-Hydroxy-4,5-dimethoxybenzaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(benzyloxy)-4,5-dimethoxybenzaldehyde (246, 5.05 g, 18.6 mmol) in ethyl acetate (100 mL) was added 10% palladium on charcoal (250 mg). The flask was purged with hydrogen and then the reaction mixture was stirred under a hydrogen atmosphere (1 atm) for 15 hours, filtered through a celite pad, the filtrate was evaporated under reduced pressure, and the resulting solid dried under vacuum to afford 243b as a white solid (3.3 g, 98% yield). 1H NMR: (DMSO) δ 11.39 (s, 1H), 9.68 (s, 1H), 6.90 (d, J=2.5 Hz, 1H), 6.47 (s, 1H), 3.94 (s, 3H), 3.89 (s, 3H).

Workup

  1. customThe flask was purged with hydrogen
  2. filtrationfiltered through a celite pad
  3. customthe filtrate was evaporated under reduced pressure
  4. customthe resulting solid dried under vacuum

Sources & evidence

ORD record
ord-f87601ad2de748f68d06add419b68d17
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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