1-Propanol → n-Propyl-4-chloro-3,5-dinitro-benzoate
Reaction equation
[CH2:1]([O:4][C:5](=[O:25])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9](N(CC=C)CC=C)=[C:8]([N+:22]([O-:24])=[O:23])[CH:7]=1)[CH2:2][CH3:3].[Cl:26]C1C([N+]([O-])=O)=CC(C(O)=O)=CC=1[N+]([O-])=O.C(O)CC>S(=O)(=O)(O)O.O>[CH2:1]([O:4][C:5](=[O:25])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[C:9]([Cl:26])=[C:8]([N+:22]([O-:24])=[O:23])[CH:7]=1)[CH2:2][CH3:3]Participants
Procedure
According to a preferred form of realization of the process of the present invention n-propyl-4-diallylamino-3,5-dinitro-benzoate may be prepared by reacting 1 mole of 4-chloro-3,5-dinitro-benzoic acid with 1.25 moles of n-propanol at a temperature between 85° C. and 90° C., in the presence of a sulfuric acid catalyst, whereby the water formed is removed by azeotropic distillation with benzene. The distillation of water having been completed (5-7 hours) the reaction mixture, is cooled and the n-propyl-4-chloro-3,5-dinitro-benzoate is isolated. This compound is reacted with a 1.1 molar amount of diallyl amine at a temperature between 70° C. and 80° C., in an aqueous melt in the presence of 0.1 mole of 75% phosphoric acid and 1.05 moles of a 10% sodium hydroxide solution as acid binding agent. The reaction mixture is allowed to sedimentate, the organic phase is poured into water and the crystalline n-propyl-4-diallylamino-3,5-dinitro-benzoate is isolated.
Workup
- custommay be prepared
- customat a temperature between 85° C. and 90° C.
- customis removed by azeotropic distillation with benzene
- distillationThe distillation of water having
- custom(5-7 hours)
- temperatureis cooled
Sources & evidence
- ORD record
- ord-8371264fcf434420b4614a8e5c48ec21
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04806151
Reaction notes
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