Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[CH:6]=[C:7]([O:11]C)[C:8]=1[O:9][CH3:10].C1(C)C=CC(S(O)(=O)=[O:21])=CC=1.OO.[N+]([O-])(O)=O>C(O)(=O)C.O>[CH3:10][O:9][C:8]1[C:7](=[O:11])[CH:6]=[C:5]([CH3:13])[C:4](=[O:21])[C:3]=1[O:2][CH3:1]Participants
Procedure
3,4,5-Trimethoxy toluene (18.2 g, MW 182.21, 0.1 mol), para-toluene sulphonic acid (1.7 g, MW 172.13, 0.01 mol) are dissolved in glacial acetic acid to give a total volume of 50 ml and the solution is connected to the pump 1. Hydrogen peroxide (0.2 mol, MW 34.02, 21.6 ml if H2O2 at 30% and 17.5 ml if H2O2 at 35%) diluted to 50 ml with glacial acetic acid is connected to the pump 1 (second tube). The nitric acid (90%, 0.05 mol, MW 63.02, d 1.49, 3.15 g, 3.5 g solution 90%, 2.35 ml solution 90%) dissolved in acetic acid (to 50 ml) is connected to the pump 2. The pump 1 is pumping approximately 3.8 ml/min for each of the two reagent solutions (total speed flow 7.6 ml/min, i.e. 38 ml reactor volume/5 min RT). Isoversinic tubes (ID 2 mm) was used on the peristaltic pump. The residence time of the reaction was about 5 min (38 ml volume reactor) and the reaction was performed at 75° C. pumping the solutions of the pumps 1. After 5 min the nitric acid solution was pumped at 3.8 ml/min into the second section of the reactor (11 ml, volume reactor) cooled by a cold water circuit.
Workup
- customto give a total volume of 50 ml
- customof the two reagent solutions (total speed flow 7.6 ml/min, i.e. 38 ml reactor volume/5 min RT)
- customwas performed at 75° C.
Sources & evidence
- ORD record
- ord-97df86aa7f294645abeafc1d54470d7c
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528271B2
Linked notes
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