Nitric Acid → 2,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-
Reaction equation
C(Cl)(Cl)(Cl)Cl.[CH3:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]([CH3:14])[C:8]=1[OH:15].ClCl.[N+]([O-])(O)=[O:19]>O>[CH3:6][C:7]1[C:8](=[O:15])[C:9]([CH3:14])=[CH:10][C:11](=[O:19])[C:12]=1[CH3:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
1000 g of carbon tetrachloride was charged in a 5-liter four neck flask equipped with a stirrer, a condenser, a chlorine-bubbling pipe and a thermometer, and 408 g (3 moles) of 2,3,6-trimethylphenol was dissolved therein. Thereafter, 210 g (3 moles) of chlorine gas was bubbled thereinto at 40°C in 2 hours. After the completion of the bubbling, a mixture of 210 g of a commercially available nitric acid (63 percent by weight) and 600 g of water was immediately added dropwise thereto at 40°C for 2 hours. After the completion of the dropwise addition, the stirring was continued for further 1 hour. Then, the reaction solution was allowed to stand, and the separated lower layer of carbon tetrachloride was taken out, and washed with water, followed by distilling off carbon tetrachloride. Thus, 460 g of the residue was obtained as a red oil, in which 405 g of 2,3,6-trimethyl-p-benzoquinone was included. (90 percent in yield).
Workup
- customequipped with a stirrer, a condenser
- customa chlorine-bubbling pipe
- additionwas immediately added dropwise
- waitat 40°C for 2 hours
- additionAfter the completion of the dropwise addition
- waitthe stirring was continued for further 1 hour
- customthe separated lower layer of carbon tetrachloride
- washwashed with water
- distillationby distilling off carbon tetrachloride
Sources & evidence
- ORD record
- ord-f22e57caa8ab432293ff57a64d822410
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03932475
Reaction notes
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