Nitroethane → HCID 12275568, compound

HRID 1944194Notes

Reaction equation

HRID 1944194 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:24]([CH2:27][CH3:28])([O-:26])=[O:25]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11](/[CH:12]=[C:27](/[N+:24]([O-:26])=[O:25])\[CH3:28])[CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 12275568HCID 12275568, compoundYield 63%

Procedure

3-Benzyloxy-4-methoxybenzaldehyde (8.0 g, 33.05 mmol), ammonium acetate (2.55 g, 33.05 mmol) and nitroethane (120 ml) were stirred under reflux for 22 h. The reaction mixture was cooled to rt and nitroethane was removed in vacuo. The solid residue was dissolved in ethyl acetate (200 ml), washed with water (40 ml) and brine (2×40 ml), dried (MgSO4) and concentrated in vacuo. Recrystallisation from ethanol afforded the title compound (6.19 g, 63%) as yellow crystals. mp=102-104° C. 1H NMR (270 MHz; CDCl3) 2.27 (3H, s, CH3), 3.94 (3H, s, OCH3), 5.19 (2H, s, CH2Ph), 6.91 (1H, d, J=2.0 Hz, CH), 6.94 (1H, d, J=8.4 Hz, CH), 7.05 (1H, dd, J=8.4, 2.0 Hz, CH), 7.30-7.43 (4H, m, 4×CH), 7.97 (1H, s, CH). 13C NMR (67.5 MHz; CDCl3) 14.03 (CH3), 56.15 (OCH3), 71.25 (CH2Ph), 111.69 (CH), 115.77 (CH), 124.93 (C), 124.94 (CH), 127.16 (CH), 128.19 (CH), 128.83 (CH), 133.84 (CH), 136.65 (C), 145.92 (C), 148.00 (C), 151.51 (C). LC/MS (APCI−) tr=1.07 min, m/z 297.93 (M−H)−.

Workup

  1. temperatureunder reflux for 22 h
  2. customnitroethane was removed in vacuo
  3. dissolutionThe solid residue was dissolved in ethyl acetate (200 ml)
  4. washwashed with water (40 ml) and brine (2×40 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-39958188daa64966b13d0ad0e2bcf91d
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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