反应详情

To a solution of (3-hydroxyphenyl)acetonitrile (75.0 g, 0.56 mol) in toluene (750 mL) was added paraformaldehyde (84.0 g, 2.80 mol) and toluene-4-sulfonic acid monohydrate (10.7 g, 56.0 mmol) at room temperature. The reaction mixture was heated at reflux for 40 minutes. Toluene was removed by evaporation. Water (150 mL) and ethyl acetate (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was separated by preparative HPLC to give 2-(4H-benzo[d][1,3]dioxin-7-yl)acetonitrile (4.7 g, 5%). 1H NMR (300 MHz, CDCl3) δ 6.85-6.98 (m, 3H), 5.25 (d, J=3.0 Hz, 2H), 4.89 (s, 2H), 3.69 (s, 2H).

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 40 minutes
3. customToluene was removed by evaporation
4. additionWater (150 mL) and ethyl acetate (150 mL) were added
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with ethyl acetate
7. washThe combined organics were washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. customevaporated under vacuum
10. customThe residue was separated by preparative HPLC