Methanol → Methyl 3,5-dinitrobenzoate
Reaction equation
[CH3:1]O.[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([OH:11])=[O:10])([O-:5])=[O:4].S(=O)(=O)(O)O>>[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([O:11][CH3:1])=[O:10])([O-:5])=[O:4]Participants
Procedure
In a 72-liter, round-bottomed flask equipped with mechanical stirrer and condenser were combined methyl alcohol (27.97 kg, 873 moles, 35.4 liters), 3,5-dinitrobenzoic acid (15 kg, 70.72 moles), and sulfuric acid (2.6 kg, 26.56 moles, 1.42 liters). The mixture was heated and stirred at reflux by means of a heating mantle for approximately 26 hours and then was allowed to cool to 25° (approximately 18 hours). The precipated solid was isolated by centrifugation (Tolhurst 12-in. centrifuge); each of the four loads collected was washed with methyl alcohol (4 liters). The wet solid was air dried for 16-18 hours to give 14.7 kg (92% of theory) of methyl 3,5-dinitrobenzoate (I). Tlc analysis (toluene/acetone/HOAc; 90/5/2; utilizing a plate marketed by Mallinckrodt under the trade designation ChromAR 7GF plate) showed the product to be homogenous and identical to an authentic sample.
Workup
- customIn a 72-liter, round-bottomed flask equipped with mechanical stirrer and condenser
- temperatureThe mixture was heated
- temperatureat reflux by means of a heating mantle for approximately 26 hours
- temperatureto cool to 25° (approximately 18 hours)
- customThe precipated solid was isolated by centrifugation (Tolhurst 12-in. centrifuge)
- customeach of the four loads collected
- washwas washed with methyl alcohol (4 liters)
- customdried for 16-18 hours
Sources & evidence
- ORD record
- ord-0028898d638645c2ab55df520ae29460
- Source dataset
- uspto-grants-1981_08
- Patent number
- US04284620
Reaction notes
Loading…