반응 #46223

반응 방정식

(4-hydroxyphenyl)acetonitrile

paraformaldehyde

toluene-4-sulfonic acid monohydrate

→

2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 1 hour
3. 3
   기타Toluene was removed by evaporation
4. 4
   workup.ADDITIONWater (150 mL) and ethyl acetate (150 mL) were added
5. 5
   기타The organic layer was separated
6. 6
   추출the aqueous layer was extracted with ethyl acetate
7. 7
   세척The combined organics were washed with brine
8. 8
   건조dried over Na2SO4
9. 9
   기타evaporated under vacuum
10. 10
    기타The residue was separated by preparative HPLC

실험 절차

To a solution of (4-hydroxyphenyl)acetonitrile (17.3 g, 0.13 mol) in toluene (350 mL) were added paraformaldehyde (39.0 g, 0.43 mmol) and toluene-4-sulfonic acid monohydrate (2.5 g, 13 mmol) at room temperature. The reaction mixture was heated at reflux for 1 hour. 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 Na2SO4 and evaporated under vacuum. The residue was separated by preparative HPLC to give 2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile (7.35 g, 32%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.11 (m, 1H), 6.95-6.95 (m, 1H), 6.88 (d, J=11.6 Hz, 1H), 5.24 (s, 2H), 4.89 (s, 2H), 3.67 (s, 2H).

출처