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

HRID 54586

Reaction equation

HRID 54586 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-24bd5505bcae4988aed129c6132f0ea9
Source dataset
uspto-grants-1997_04
Patent number
US05622987

Linked notes

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