Water → 2-(3-Nitrobenzylidene)-3,4-dihydronaphthalen-1(2h)-one

HRID 1376916Notes

Reaction equation

HRID 1376916 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 74493-NitrobenzaldehydeHCID 107241-TetraloneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 2888042-(3-Nitrobenzylidene)-3,4-dihydronaphthalen-1(2h)-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,4-dihydro-1(2H)-naphthalenone (21.9 G), 3-nitrobenzaldehyde (22.6 g) and p-toluenesulphonic acid monohydrate (50 mg) in toluene (250 ml) was stirred at reflux with separation of water for 4.5 hours. The brown solution was allowed to cool overnight. The resulting yellow-orange deposited solid was filtered off, washed well with toluene and dried in vacuo yielding 2-(3-nitrobenzylidene)-3,4-dihydro-1(2H)-naphthalenone as crisp yellow needles.

Workup

  1. temperatureto cool overnight
  2. filtrationwas filtered off
  3. washwashed well with toluene
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a537eaefdb544136b880ca0a3f5b478c
Source dataset
uspto-grants-1997_09
Patent number
US05663375

Reaction notes

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