2-Benzyloxy-3,4-dimethoxybenzonitrile → 2-Hydroxy-3,4-dimethoxybenzonitrile

HRID 2228507Notes

Reaction equation

HRID 2228507 reaction equation
C([O:8][C:9]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1>[Pd].C(O)C>[OH:8][C:9]1[C:16]([O:17][CH3:18])=[C:15]([O:19][CH3:20])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 1

HCID 184706112-Benzyloxy-3,4-dimethoxybenzonitrile

Product 1

HCID 119947582-Hydroxy-3,4-dimethoxybenzonitrileYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on charcoal (2.0 g) was added to a solution of 2-benzyloxy-3,4-dimethoxybenzonitrile (20.8 g, 0.077 mol) in ethanol (250 ml) and the reaction stirred under a hydrogen atmosphere of 414 kPa (60 p.s.i.) for 4 hours. On cooling, the mixture was filtered through Arbocel™, washing with further ethanol. The filtrate was evaporated under reduced pressure to give the subtitle compound as a yellow solid (13.37 g, 97%). Rf 0.19 (dichloromethane). MS m/z 197 (MNH4)+.

Workup

  1. temperatureOn cooling
  2. filtrationthe mixture was filtered through Arbocel™
  3. washwashing with further ethanol
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6cbe3970b6884e909c76703a8dd8bf4b
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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