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

HRID 2307156Notes

Reaction equation

HRID 2307156 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-170540862f394c6597b36238bf3f8ac1
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

Loading…