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

HRID 2307164Notes

Reaction equation

HRID 2307164 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[CH2:19][CH2:18][C:17](=[O:20])[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[CH2:19][CH2:18][C:17](=[O:20])[CH2:16]1

Participants

3

Reactant 1

HCID 22337807(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclopentanone

Product 1

HCID 22337821(+/-)-3-(2,4-Dihydroxyphenyl)cyclopentanoneYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclopentanone (8 mg) was heated at 50° C. in MeOH (3 ml) containing acidic ion exchange resin (0.1 g) for 3 hr. The reaction mixture was filtered and the resin washed with ethyl acetate (20 ml). The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, ethyl acetate) to furnish the title compound as a white solid (3.8 mg, 70%). δH (d4-MeOH) 2.52-2.13 (1H, m), 2.26-2.48 (4H, overlapping m), 2.53-2.60 (1H, m), 3.55-3.61 (1H, m), 6.29 (1H, dd), 6.33 (1H, d), 6.96 (1H, d); m/z (ES−) 251 ((M+60)−1)−.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resin washed with ethyl acetate (20 ml)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash column chromatography (SiO2, ethyl acetate)

Sources & evidence

ORD record
ord-18efec8ba2dd4cdfbbda717299e34960
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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