Water → Ethyl-m-nitrocinnamate

HRID 1256080Notes

Reaction equation

HRID 1256080 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([O:14][C:15](=[O:25])[CH2:16]P(OCC)(OCC)=O)[CH3:13].[H-].[Na+].O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:16][C:15]([O:14][CH2:12][CH3:13])=[O:25])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Product 1

HCID 94827Ethyl-m-nitrocinnamateYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-nitrobenzaldehyde (49 g, 295 mmol) and (diethoxy-phosphoryl)-acetic acid ethyl ester (72.74 g, 325 mmol) in DMF (300 ml) at 0° C. was added NaH (14.2 g, 354 mmol) portionwise and stirred for 1.5 hrs at r.t. The reaction mixture was poured into water to give colorless crystals, which were collected by filtration and washed with water and hexane to give the product ethyl 3-(3-nitrophenyl)acrylate (63 g, yield 96.6%). 1H NMR MeOD 400 MHz. δ 8.42-7.62 (m, 4H), 7.74-7.70 (d, 1H), 6.68-6.64 (d, 1H), 4.28-4.22 (m, 2H), 1.34-1.30 (m, 3H).

Workup

  1. customto give colorless crystals, which
  2. filtrationwere collected by filtration
  3. washwashed with water and hexane

Sources & evidence

ORD record
ord-bd0fdc0f03f3443c8d05728335aaed51
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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