1-Nitropropane → HCID 2826291, compound

HRID 1944217Notes

Reaction equation

HRID 1944217 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][CH2:28][CH3:29])([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])[CH2:28][CH3:29])[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 79031-NitropropaneHCID 806713-Benzyloxy-4-methoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2826291HCID 2826291, compoundYield 44.9%

Conditions

Temperature
160 °C

Procedure

3-Benzyloxy-4-methoxybenzaldehyde (24.23 g, 100 mmol) and ammonium acetate (7.73 g, 100 mmol) were covered with 1-nitropropane (90 mL, 1008 mmol) and heated to 160° C. for 22 h. The reaction mixture was then cooled to room temperature and the excess of 1-nitropropane was removed in vacuo. The residue was dissolved in ethyl acetate (300 mL), washed with water (100 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was boiled up in ethanol (100 mL). After cooling to room temperature the yellow precipitate was collected on a sinter funnel and washed with ethanol (4×30 mL). The solid was dried in vacuo to give the title compound as yellow powder (14.07 g, 44%). 1H NMR (270 MHz, CDCl3) δ 1.14 (3H, t, J 7.3, CH2CH3), 2.71 (2H, q, J 7.4, CH2CH3), 3.93 (3H, s, OCH3), 5.19 (2H, s, OCH2Ph), 6.91 (1H, d, J 1.9, CH), 6.94 (1H, d, J 8.5, CH), 7.05 (1H, dd, J 8.4, CH), 7.25-7.48 (5H, m, OCH2C6H5), 7.91 (1H, s, HC═CNO2).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe excess of 1-nitropropane was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  4. washwashed with water (100 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. temperatureAfter cooling to room temperature the yellow precipitate
  9. customwas collected on a sinter funnel
  10. washwashed with ethanol (4×30 mL)
  11. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-d540827816164fdf84b34fc9ad409e06
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

Loading…