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

HRID 439344Notes

Reaction equation

HRID 439344 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 resultant orange-yellow solid filtered off, washed with toluene and dried in vacuo to give 2-(3-nitrobenzylidene)-3,4-dihydro-1(2H)-naphthalenone as yellow needles.

Workup

  1. temperatureto cool overnight
  2. filtrationthe resultant orange-yellow solid filtered off
  3. washwashed with toluene
  4. customdried in vacuo

Sources & evidence

ORD record
ord-97c9f541abb540088d0d2141bdecb3de
Source dataset
uspto-grants-1996_05
Patent number
US05514699

Reaction notes

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