(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone → (+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanone

HRID 2307152Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone (35 mg) in methanol (4 ml) containing acidic ion exchange resin (300 mg) was stirred at 50° C. for 6 hr, and then at ambient temperature for 16 hr. The mixture was evaporated in vacuo and the residue was redissolved in acetone (4 ml) containing water (2 drops) and stirred at 50° C. for 8 hr, then at ambient temperature for 64 hr. The mixture was filtered through celite and purified by flash column chromatography (SiO2, petroleum ether/ethyl acetate 1:1 v/v) to furnish the title compound as a white solid containing an equilibrium mixture of cyclized and uncyclized forms (31 mg, 76%). δH (DMSO) 1.1-2.3 (8H, overlapping m), 3.0 (1H, m), 6.08 (0.5H, bs), 6.16 (1H, bd), 6.25 (0.5H, bs), 6.53 (0.5H, bs), 6.75 (0.5H, d), 6.89 (0.5H, b), 8.98 (0.5H, bs), 9.02 (0.5H, bs), 9.17 (0.5H, bs); m/z (ES−) 205 (M−H)−.

Workup

waitat ambient temperature for 16 hr
customThe mixture was evaporated in vacuo
dissolutionthe residue was redissolved in acetone (4 ml)
additioncontaining water (2 drops)
stirringstirred at 50° C. for 8 hr
waitat ambient temperature for 64 hr
filtrationThe mixture was filtered through celite
custompurified by flash column chromatography (SiO2, petroleum ether/ethyl acetate 1:1 v/v)

Sources & evidence

ORD record: ord-04d2488cf4c44f6e93e22eef9456679f
Source dataset: uspto-grants-2004_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06828460B2

Reaction notes

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