2-(2-Benzyloxy-5-methoxymethoxyphenyl)acetonitrile → 2-(2-Hydroxy-5-methoxymethoxyphenyl)acetonitrile

HRID 1294106Notes

Reaction equation

HRID 1294106 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][C:10]=1[CH2:19][C:20]#[N:21])C1C=CC=CC=1>[C].[Pd].O1CCCC1>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][O:17][CH3:18])=[CH:11][C:10]=1[CH2:19][C:20]#[N:21]

Participants

4

Reactant 1

HCID 178612212-(2-Benzyloxy-5-methoxymethoxyphenyl)acetonitrile

Product 1

HCID 178612602-(2-Hydroxy-5-methoxymethoxyphenyl)acetonitrileYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2-benzyloxy-5-methoxymethoxyphenyl)acetonitrile (2.95 g), 5% palladium carbon (2.0 g) and tetrahydrofuran (100 mL) was subjected to catalytic hydrogenation at room temperature and 4.8 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure to give crystals (1.88 g, 94%) of 2-(2-hydroxy-5-methoxymethoxyphenyl)acetonitrile. Recrystallization from ethyl acetate-hexane gave pale-brown prism crystals. melting point: 68-69° C.

Workup

  1. customwas subjected to catalytic hydrogenation at room temperature
  2. filtrationAfter filtering off the catalyst
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b1a39ce74c33403f9008ab87a20983be
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…