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

HRID 2307173Notes

Reaction equation

HRID 2307173 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]([C:21]([NH2:23])=[O:22])[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][CH:17]([C:21]([NH2:23])=[O:22])[CH2:16]1

Participants

3

Reactant 1

HCID 22337819(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide

Product 1

HCID 22337782(+/-)-3-(2,4-Dihydroxyphenyl)cyclohexanecarboxamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanecarboxamide (22 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated to reflux for 5 hr. The reaction mixture was filtered and the resin was washed with methanol. The combined filtrate and washings were evaporated in vacuo and the crude residue was purified by preparative HPLC to give the title compound as a white solid (5 mg, 31%). δH(CD3OD) 1.45-1.82 (6H, m), 2.07-2.19 (2H, m), 2.62-2.69 (1H, m), 3.00-3.09 (1H, m), 6.20-6.28 (2H, m), 6.89 (1H, d); m/z (ES+) 236 (M+H)+.

Workup

  1. temperatureto reflux for 5 hr
  2. filtrationThe reaction mixture was filtered
  3. washthe resin was washed with methanol
  4. customThe combined filtrate and washings were evaporated in vacuo
  5. customthe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-22eb919ac6a64676997a8de0ca9711e6
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

Loading…