3-Nitrobenzaldehyde → Ethyl-m-nitrocinnamate

HRID 1696464Notes

Reaction equation

HRID 1696464 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:36])[CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:13]>C(Cl)Cl>[CH2:12]([O:14][C:15](=[O:36])[CH:16]=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:13]

Participants

4

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 94827Ethyl-m-nitrocinnamateYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-nitro-benzaldehyde (15.1 g, 0.1 mol) in CH2Cl2 (200 mL) was added dropwise (triphenyl-phosphanylidene)acetic acid ethyl ester (34.8 g, 0.1 mol) in CH2Cl2 (100 mL) at 0° C. After the addition was complete, the resulting mixture was stirred for 1 h. After removal the solvent under reduced pressure, the residue was purified by column chromatography to afford 3-(3-nitrophenyl)acrylic acid ethyl ester (16.5 g, 74.6% yield). 1H NMR (400 MHz, CDCl3): δ 8.42 (s, 1H), 8.23 (dd, J=0.8, and 8.0 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H), 7.72 (d, J=16.0 Hz, 1H), 7.58 (t, J=8.0 Hz, 1H), 6.56 (d, J=16.0 Hz, 1H), 4.29 (q, J=7.2 Hz, 2H), 1.36 (t, J=6.8 Hz, 3H).

Workup

  1. additionAfter the addition
  2. customAfter removal the solvent under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-88be401b007a42aa817e2844e3e062dd
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…