反应详情

2-Methyl[1,1'-biphenyl]-3-methanol was prepared as follows: To 100 ml of stirred 50% aqueous ethanol was added 2-methyl-3-nitrobenzyl alcohol (41.8 g, 0.25 mole) and 85.0 grams of iron powder. The mixture was brought to reflux, and 5.2 ml of concentrated hydrochloric acid was slowly added. Upon complete addition, the reaction mixture was stirred under reflux for 2 hours. The reaction mixture was then made just basic with ethanolic 15% potassium hydroxide. The hot mixture was filtered through diatomaceous earth to remove the iron. The filter cake was washed with ethanol. The filtrate was acidified with hydrogen chloride, then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure. Hexane was added to the residue, and the water-hexane azeotrope was removed by distillation. The addition of hexane and the subsequent removal of the water-hexane azeotrope by distillation was repeated three times. The 3-hydroxymethyl-2-methylaniline hydrochloride residue thus obtained was used as follows.

1. temperatureto reflux
2. additionUpon complete addition
3. temperatureunder reflux for 2 hours
4. filtrationThe hot mixture was filtered through diatomaceous earth
5. customto remove the iron
6. washThe filter cake was washed with ethanol
7. customThe ethanol was removed by evaporation under reduced pressure
8. additionHexane was added to the residue
9. customthe water-hexane azeotrope was removed by distillation
10. additionThe addition of hexane
11. customthe subsequent removal of the water-hexane azeotrope
12. distillationby distillation