(+/-)-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanol → (+/-)-4-[3-(Hydroxymethyl)cyclohexyl]-1,3-benzenediol

HRID 585694Notes

Reaction equation

HRID 585694 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][CH:17]([CH2:21][OH:22])[CH2:16]1>CO>[OH:22][CH2:21][CH:17]1[CH2:18][CH2:19][CH2:20][CH:15]([C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[OH:4])[CH2:16]1

Participants

3

Reactant 1

HCID 22337773(+/-)-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanol

Product 1

HCID 20824672(+/-)-4-[3-(Hydroxymethyl)cyclohexyl]-1,3-benzenediolYield 8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-{3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexyl}methanol (35 mg) was heated at 50° C. in methanol (3.5 ml) containing acidic ion exchange resin (350 mg). After 6 hr, the mixture was filtered, the resin was washed with ethyl acetate, and the combined filtrate and washings were evaporated in vacuo. The crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v) to furnish a mixture of diastereoisomers of the title compound as a white solid (2 mg, 8%). δH (d4-MeOH) 0.9-1.9 (9H, overlapping m), 2.80 (0.5H, m), 2.90 (0.5H, m), 3.20-3.40 (2H, overlapping m), 6.15 (2H, m), 6.80 (0.5H, d), 6.85 (0.5H, d); m/z (ES−) 221 (M−H)−.

Workup

  1. filtrationthe mixture was filtered
  2. washthe resin was washed with ethyl acetate
  3. customthe combined filtrate and washings were evaporated in vacuo
  4. customThe crude residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:1 v/v)
  5. customto furnish

Sources & evidence

ORD record
ord-13f3daab70f145dcb9bd5e09e047cd48
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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