Benzyl 2-[4-(2-methoxyphenyl)-1-butenyl]phenyl ether → 2-[4-(2-Methoxyphenyl)butyl]phenol

HRID 743387Notes

Reaction equation

HRID 743387 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19]CC1C=CC=CC=1>C(O)C.[H][H].[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19]

Participants

5

Reactant 1

HCID 67667339Benzyl 2-[4-(2-methoxyphenyl)-1-butenyl]phenyl ether

Product 1

HCID 194239792-[4-(2-Methoxyphenyl)butyl]phenolYield 60%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 23938PalladiumSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Following a procedure similar to that described in the latter part of Preparation 3, the whole of the benzyl 2-[4-(2-methoxyphenyl)-1-butenyl]phenyl ether prepared as described above was dissolved in 50 ml of ethanol and hydrogenated at 50° C. in an atmosphere of hydrogen at atmospheric pressure and in the presence of 100 mg of 5% w/w palladium-on-charcoal for 6 hours. The crude product thus obtained was purified by column chromatography through silica gel, using 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.44 g (yield 60%) of the title compound as a colorless oil.

Workup

  1. customthat described in the latter part of Preparation 3
  2. customThe crude product thus obtained
  3. customwas purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-2b23264ec9294908b1df8c2d52871c46
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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