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

HRID 585713Notes

Reaction equation

HRID 585713 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]([NH:23][CH2:24][CH3:25])=[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]([NH:23][CH2:24][CH3:25])=[O:22])[CH2:16]1

Participants

3

Reactant 1

HCID 22337779(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide

Product 1

HCID 22337813(+/-)-3-(2,4-Dihydroxyphenyl)-N-ethylcyclohexanecarboxamideYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(±)-3-[2,4-Bis(methoxymethoxy)phenyl]-N-ethylcyclohexanecarboxamide (25 mg), methanol (2 ml) and acidic ion exchange resin (300 mg) were heated to reflux for 4 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 furnish the title compound as a solid (2 mg, 12%). δH (CD3OD) 1.80 (3H, t), 1.30-1.60 (4H, m), 1.74-1.94 (4H, m), 2.26-2.36 (1H, m), 2.82-2.92 (1H, m), 3.16 (2H, q), 6.21-6.26 (2H, m), 6.88 (1H, d); m/z (ES+) 264 (M+H)+.

Workup

  1. temperatureto reflux for 4 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-8ff26086e2c74c47b07c0f738bb12e14
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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