Hydroquinone → Bicyclo[2.2.1]hept-5-ene-2-methanol, 2-acetate
Reaction equation
[CH2:1]1[CH:5]2[CH:6]3[CH:10]=[CH:9][CH:8]([CH:4]2C=C1)[CH2:7]3.[C:11]([O:14]CC=C)(=[O:13])[CH3:12].C1(C=CC(O)=CC=1)O>>[C:11]([O:14][CH2:1][CH:5]1[CH2:4][CH:8]2[CH2:7][CH:6]1[CH:10]=[CH:9]2)(=[O:13])[CH3:12]Participants
4
Conditions
- Temperature
- 180 °C
Procedure
Dicyclopentadiene 1094 g (manufactured by Wako Pure Chemical Industries, Ltd.), 1772 g of allyl acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 1 g of hydroquinone (manufactured by Wako Pure Chemical Industries, Ltd.) were placed into an autoclave, and a space was replaced by nitrogen. The mixture was stirred at an internal temperature of 180° C. in a sealed system for 9 hours (rotating speed=300 rpm). The reaction mixture was filtered, and volatile components were evaporated. The residue was subjected to precision distillation (length of column=120 cm, filler=Propak, reflux ratio=10/1, pressure=10 mmHg, trap temperature=89° C.), thereby obtaining colorless and transparent NBCH2OCOCH3. The peak purity thereof was measured by gas chromatography, and the NBCH2OCOCH3 has the purity of 99.9% and endo/exo ratio of 83/17.