Nitromethane → 1,2-Benzenediol, 4-(2-nitroethenyl)-

HRID 38314

Reaction equation

HRID 38314 reaction equation
C([O-])(=O)C.[NH4+].[OH:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[OH:15])[CH:10]=O.[N+:16]([CH3:19])([O-:18])=[O:17]>>[N+:16]([CH:19]=[CH:10][C:9]1[CH:8]=[C:7]([OH:6])[C:14]([OH:15])=[CH:13][CH:12]=1)([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 87683,4-DihydroxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 54872581,2-Benzenediol, 4-(2-nitroethenyl)-Yield 61%

Procedure

Ammonium acetate (5.6 g, 72.73 mmol, 1.00 equiv) was added to a solution of 3,4-dihydroxybenzaldehyde (10 g, 72.41 mmol, 1.00 equiv) and nitromethane (50 mL). The resulting mixture was heated at reflux for about 16 hours, and then concentrated in vacuo. The resulting residue was then purified by silica gel column chromotagraphy (ethyl acetate/petroleum ether (1:5)) to give the title compound as a yellow oil (8 g, yield=61%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for about 16 hours
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was then purified by silica gel column chromotagraphy (ethyl acetate/petroleum ether (1:5))

Sources & evidence

ORD record
ord-948b2595e32c48ddb6b3bc450387cff4
Source dataset
uspto-grants-2013_09
Patent number
US08524733B2

Linked notes

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