1-Benzyloxy-4-(2-methoxyethoxy)benzene → 4-(2-Methoxyethoxy)phenol

HRID 580974Notes

Reaction equation

HRID 580974 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[CH3:19][O:18][CH2:17][CH2:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 133135851-Benzyloxy-4-(2-methoxyethoxy)benzene

Product 1

HCID 133135614-(2-Methoxyethoxy)phenolYield 80.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(benzyloxy)-4-(2-methoxyethoxy)benzene (180 g), ethanol (2000 ml) and palladium on carbon catalyst (20 g) was stirred under an atmosphere of hydrogen, at room temperature and atmospheric pressure. After the theoretical quantity of hydrogen had been consumed, the reaction mixture was filtered. The filtrate was evaporated to give a solid which was crystallised from a mixture of ethyl acetate and n-hexane to give 4-(2-methoxyethoxy)phenol as a solid (94.7 g) m.p. 97.9° C.; microanalysis, found: C, 64.3%; H, 7.4%; C9H12O3 requires: C, 64.3%; H, 7.2%; NMR: 3.35(3H,s), 3.6(2H,m), 3.95(2H,m), 6.7(4H,m) and 8.9(1H,s); m/z 169(M+H).

Workup

  1. customAfter the theoretical quantity of hydrogen had been consumed
  2. filtrationthe reaction mixture was filtered
  3. customThe filtrate was evaporated
  4. customto give a solid which
  5. customwas crystallised from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-769281acd38042f988026185e71a313c
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

Loading…