4,4 Inverted exclamation mark-dihydroxystilbene → 1,2-Bis(4-hydroxyphenyl)ethane

HRID 2260949Notes

Reaction equation

HRID 2260949 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1>CO.CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 928304,4 Inverted exclamation mark-dihydroxystilbene

Product 1

HCID 801521,2-Bis(4-hydroxyphenyl)ethaneYield 97.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4′-dihydroxystilbene (250 mg, 1.178 mmol) in MeOH (10 mL) and EtOAc (2 mL) containing 5% Pd-C (120 mg) was stirred under an atmosphere of hydrogen for 2 h. The catalyst was removed by filtration and the filtrate was concentrated. Chromatography purification of the crude product on silica gel (hexane-EtOAc 3:1, 2;1) provided 245 mg of 4-[4-Hydroxy-phenethyl]-phenol (97%) as a white solid. MS (ES) m/z: 213.05 (M−1).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customChromatography purification of the crude product on silica gel (hexane-EtOAc 3:1, 2;1)

Sources & evidence

ORD record
ord-89ea99b03fd94aa8b39650ce061cf2e2
Source dataset
uspto-grants-2010_12
Patent number
US07846915B2

Reaction notes

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