تفاعل #46223

معادلة التفاعل

(4-hydroxyphenyl)acetonitrile

paraformaldehyde

toluene-4-sulfonic acid monohydrate

→

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

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was heated
2. 2
   درجة الحرارةat reflux for 1 hour
3. 3
   أخرىToluene was removed by evaporation
4. 4
   workup.ADDITIONWater (150 mL) and ethyl acetate (150 mL) were added
5. 5
   أخرىThe organic layer was separated
6. 6
   استخلاصthe aqueous layer was extracted with ethyl acetate
7. 7
   غسيلThe combined organics were washed with brine
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىevaporated under vacuum
10. 10
    أخرىThe residue was separated by preparative HPLC

الإجراء التجريبي

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).

المصدر