Benzene → HCID 57725029, compound

Reaction equation

[N+:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][CH3:19])([CH3:16])[CH2:8][CH:7]2O)([O-:3])=[O:2].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[N+:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][CH3:19])([CH3:16])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

Procedure

To 10.1 g of 6-nitro-4-hydroxy-2-methoxymethyl-2,5,7,8-tetramethylchroman, 200 ml of benzene was added and 1.0 g of p-toluenesulfonic acid was added, followed by heating at reflux for 2 hours using a Dean-Stark apparatus. The reaction solution was poured into water and then extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, 9.4 g of the objective oily compound was obtained.