反应详情

温度

5 °C

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (18.2 g, 0.076 mole) was added to a solution of sodium ethoxide freshly prepared from sodium (3.5 g, 0.15 mole) in ethyl alcohol (100 ml) and stirred for 1 hour. After cooling to 5° C. with an ice bath, trans-2,3-epoxybutane (5.0 g, 0.069 mole) was added and the ice bath removed. After stirring for 5.5 hours the reaction mixture was poured into ten percent hydrochloric acid (50 ml). The ethyl alcohol was removed using a rotary evaporator and the aqueous residue extracted with ethyl acetate (2×75 ml). The extracts were combined, dried over sodium sulfate, filtered, and concentrated to an orange oil. The product was purified by chromatography on silica to give a yellow solid which was recrystallized from hexane to give a white solid, m.p. ca. 73° C.

1. customthe ice bath removed
2. stirringAfter stirring for 5.5 hours the reaction mixture
3. additionwas poured into ten percent hydrochloric acid (50 ml)
4. customThe ethyl alcohol was removed
5. customa rotary evaporator
6. extractionthe aqueous residue extracted with ethyl acetate (2×75 ml)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to an orange oil
10. customThe product was purified by chromatography on silica
11. customto give a yellow solid which
12. customwas recrystallized from hexane
13. customto give a white solid, m.p. ca. 73° C.