Hydrochloric Acid → 1-Methoxy-2-methyl-4-(2-nitroethenyl)benzene

HRID 2251491Notes

Reaction equation

HRID 2251491 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[N+:12]([CH3:15])([O-:14])=[O:13].[OH-].[Na+].Cl>CO.O>[CH3:1][C:2]1[CH:3]=[C:4](/[CH:5]=[CH:15]/[N+:12]([O-:14])=[O:13])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 1229363-Methyl-4-anisaldehyde

Product 1

HCID 9584691-Methoxy-2-methyl-4-(2-nitroethenyl)benzeneYield 49%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-methyl-p-anisaldehyde (23.13 g, 154 mmol) and nitromethane (9.40 g, 154 mmol) in MeOH (260 ml) was cooled in an ice bath and treated dropwise with NaOH (162 ml of 1N solution; 162 mmol). The reaction mixture was stirred at rt for 1 hr. Water (50 ml) was then added and the mixture poured into 1N HCl (300 ml). The precipitate was collected and purified by flash chromatography on silica gel eluting with dichloromethane to provide methyl 2-methyl-4-[(E)-2-nitroethenyl]phenyl ether as a yellow solid (14.61 g; 49% yield).

Workup

  1. customThe precipitate was collected
  2. custompurified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-d10c4b1eb70040fabc515319272178ec
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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