Nitroethane → HCID 131719241, compound

HRID 374892Notes

Reaction equation

HRID 374892 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[CH:12][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=O.[N+:19]([CH2:22][CH3:23])([O-:21])=[O:20].C(N)C1C=CC=CC=1>C1(C)C=CC=CC=1>[N+:19]([C:22]([CH3:23])=[CH:1][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[CH:12][CH:13]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 7504BenzylamineHCID 18996368HCID 18996368, compound

Product 1

HCID 131719241HCID 131719241, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of one equivalent of diethyl 4-methylphthalate, two equivalents of N-bromosuccinimide and carbon tetrachloride is irradiated with a 500 W tungsten lamp for three hours. The mixture is filtered and the solution is shaken with excess sodium carbonate solution. Evaporation of the organic phase gives diethyl 4-formylphthalate. This aldehyde is combined with excess nitroethane, toluene and a catalytic amount of benzyl amine. The mixture is heated on a steam bath for 48 hours and evaporated in vacuo to give diethy 4-(2-nitropropen-1-yl)phthalate.

Workup

  1. temperatureThe mixture is heated on a steam bath for 48 hours
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-4a1777b478424c8fa5598de943f3ef37
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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