Nitroethane → HCID 69011582, compound

HRID 747383Notes

Reaction equation

HRID 747383 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([CH2:11][CH2:12][O:13][CH2:14][O:15][CH3:16])[C:8]([O:17][CH3:18])=[CH:7][C:4]=1[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:24]([CH2:27][CH3:28])([O-:26])=[O:25]>>[CH3:18][O:17][C:8]1[CH:7]=[C:4]([CH:5]=[C:27]([N+:24]([O-:26])=[O:25])[CH3:28])[C:3]([O:2][CH3:1])=[CH:10][C:9]=1[CH2:11][CH2:12][O:13][CH2:14][O:15][CH3:16]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 59749608HCID 59749608, compound

Product 1

HCID 69011582HCID 69011582, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 2,5-dimethoxy-4-(2-methoxymethoxy-ethyl)-benzaldehyde (3.00 g, 11.80 mmol) and ammonium acetate (0.91 g 11.80 mmol) in nitroethane (10 mL) was stirred at 70° C. for 2 h. After allowing the reaction mixture to cool down to room temperature, the solvent was removed under vacuum. The oily residue was purified by flash chromatography using a hexane and ethyl acetate gradient to give 0.9 g of yellow oil. MS (m/z) 211. 1HNMR(CDCl3): δ ppm 2.40 (s, 3H), 2.95 (m, 2H), 3.31 (s, 3H), 3.75 (m, 2H), 3.78 (s, 3H), 3.83 (s, 3H), 4.63 (s, 2H), 6.77 (s, 1H), 6.83 (s, 1H), 8.25 (s, 1H).

Workup

  1. temperatureto cool down to room temperature
  2. customthe solvent was removed under vacuum
  3. customThe oily residue was purified by flash chromatography

Sources & evidence

ORD record
ord-41a3b10a788643cd828eb8b04402ebd9
Source dataset
uspto-grants-2008_07
Patent number
US07396856B2

Reaction notes

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