Water → Ethyl 3-nitrocinnamate

HRID 1978394Notes

Reaction equation

HRID 1978394 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4].[N+](C1C=C(C=CC=1)C=O)([O-])=O.O>CN(C)C=O>[N+:3]([C:6]1[CH:7]=[C:8](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 86756766(E)-Ethyl 3-(3-Nitrophenyl)acrylate Sodium hydride

Product 1

HCID 5354248Ethyl 3-nitrocinnamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Synthesis of (E)-Ethyl 3-(3-Nitrophenyl)acrylate Sodium hydride (60% in oil, 2.22 g, 55.5 mmol) was added to a stirred solution of 3-nitrobenzaldehyde (8.00 g, 52.9 mmol) and triethyl phosphonoacetate (12.4 g, 55.5 mmol) in N,N-dimethylformamide (50 ml) at 0° C. After stirring at 0° C. for 1.5 hours, the reaction mixture was poured into water to give (E)-ethyl 3-(3-nitrophenyl)acrylate as colorless crystals (11.7 g, quant.), which were collected by filtration and washed with water and hexane.

Sources & evidence

ORD record
ord-a9877e53e4bb4d778a8c7430daf370fb
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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