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

HRID 585702Notes

Reaction equation

HRID 585702 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-7c3e3a0ce85e4bd98510646cbc859fca
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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