Camphor → Meta-nitrobenzylidenecamphor
Reaction equation
[C:1]12([CH3:11])[C:8]([CH3:10])([CH3:9])[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[H-].[Na+].[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=O)([O-:16])=[O:15]>C(COC)OC>[N+:14]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[C:4]1[CH:5]2[C:8]([CH3:10])([CH3:9])[C:1]([CH3:11])([CH2:7][CH2:6]2)[C:2]1=[O:3])([O-:16])=[O:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
The camphor (50.2 g, 0.33 mol), dimethoxyethane (180 ml) and sodium hydride (32 g at 50% in oil, 0.33 mol) washed with dimethoxyethane, are placed in a round-bottom flask. The mixture is heated under nitrogen to 80° C. and the meta-nitrobenzaldehyde (45.3 g, 0.3 mol) dissolved in dimethoxyethane (100 ml) is added dropwise over half an hour. The mixture is left stirring at 80° C. for 1.5 hours. The reaction mixture is allowed to cool and it is poured cautiously in 2 litres of acidified and ice cold water. The brown precipitate obtained is filtered, washed with water and dried. After recrystallisation in diisopropyl ether in the presence of vegetable black, 20 g of meta-nitrobenzylidenecamphor are obtained.
Workup
- customare placed in a round-bottom flask
- additionis added dropwise over half an hour
- waitThe mixture is left
- temperatureto cool
- additionit is poured cautiously in 2 litres
- customThe brown precipitate obtained
- filtrationis filtered
- washwashed with water
- customdried
- customAfter recrystallisation in diisopropyl ether in the presence of vegetable black, 20 g of meta-nitrobenzylidenecamphor
- customare obtained
Sources & evidence
- ORD record
- ord-e51acbb4fd5d4f5890f24057daaa7743
- Source dataset
- uspto-grants-1993_08
- Patent number
- US05236698
Reaction notes
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