3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one → 3-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-one

HRID 585689Notes

Reaction equation

HRID 585689 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=1>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=1

Participants

3

Reactant 1

HCID 121351713-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one

Product 1

HCID 121351763-(2,4-Dihydroxyphenyl)-2-cyclohexen-1-oneYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one (50 m g) was heated to 50° C. in methanol (4 ml) containing acidic ion exchange resin (500 mg). After 2 hr, the mixture was filtered and the filtrate was evaporated in vacuo and purified by flash column chromatography (SiO2, ether/petroleum ether, 9:1, v/v) to furnish the title compound as a yellow solid (31 mg, 76%). δH (DMSO) 1.95 (2H, quintet), 2.30 (2H, t), 2.69 (2H, t), 6.26 (2H, overlapping m), 6.35 (1H, m), 7.10 (1H, d), 9.67 (1H, bs), 9.86 (1H, bs); m/z (ES−) 407 (2M−H)−.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. custompurified by flash column chromatography (SiO2, ether/petroleum ether, 9:1

Sources & evidence

ORD record
ord-6cc397c1492b40c6a05fee6574a49b50
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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