3-Hydroxy-4-nitrobenzaldehyde → HCID 54189784, compound

HRID 1451634Notes

Reaction equation

HRID 1451634 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=O.[C:13]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:18][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 697123-Hydroxy-4-nitrobenzaldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

Product 1

HCID 54189784HCID 54189784, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-hydroxy-4-nitrobenzaldehyde (5 g) in toluene (50 ml) was added carbethoxymethylenetriphenylphosphorane (8.96 g), and the mixture was heated under reflux for 2 h. The mixture was then concentrated and the residue was purified by column chromatography eluting with cyclohexane:ethyl acetate (6:4) to give the title compound. (6.2 g) as a solid, m.p. 95°.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was then concentrated
  4. customthe residue was purified by column chromatography
  5. washeluting with cyclohexane:ethyl acetate (6:4)

Sources & evidence

ORD record
ord-d13dbf9f6aae4890a1b7c108ae1c0aa6
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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