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

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

Reactant 3

HCID 6375Nitromethane

HCID 87683,4-Dihydroxybenzaldehyde

HCID 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

temperatureThe resulting mixture was heated
temperatureat reflux for about 16 hours
concentrationconcentrated in vacuo
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
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524733B2

Reaction notes

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