反应详情

To an ether solution of phenylmagnesium bromide [prepared from bromobenzene (3.69 ml, 35 m mol), magnesium (0.95 g, 39 m mol) and ether (50 ml)], an ether solution (30 ml) of 3-ethoxybenzaldehyde (3.0 g, 20 m mol) was added dropwise thereto with stirring and under cooling with ice. After 30 minutes, 1 N hydrochloric acid (20 ml) was added thereto. The ether layer was separated and the aqueous layer was extracted with ether (20 ml). After the combined ether layer was washed with a saturated aqueous solution of sodium chloride (15 ml) and dried, the solvent was distilled off under reduced pressure. The resulting residue was subjected to chromatography on silica gel (100 g) using hexane, and eluted with hexane and then with hexane-ethyl acetate (5:1). The resulting yellow oily material containing the desired compound was distilled to obtain the desired compound (2.9 g, 60%) as a colorless oily material (150-153° C./1-2 mmHg).

1. temperatureunder cooling with ice
2. customThe ether layer was separated
3. extractionthe aqueous layer was extracted with ether (20 ml)
4. washAfter the combined ether layer was washed with a saturated aqueous solution of sodium chloride (15 ml)
5. customdried
6. distillationthe solvent was distilled off under reduced pressure
7. washeluted with hexane
8. additionThe resulting yellow oily material containing the desired compound
9. distillationwas distilled