تفاعل #344474

معادلة التفاعل

phenol

4-(4-Hydroxyphenyl)benzonitrile

Potassium tert-butoxide

Allyl bromide

→

white crystalline material

المردود 65.0%

4-(4-Allyloxyphenyl)benzonitrile

المردود 65.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded to a 500-mL 3-neck round-bottom flask
2. 2
   درجة الحرارةthe mixture was refluxed overnight
3. 3
   أخرىThe THF and allyl bromide were removed by rotoevaporation
4. 4
   استخلاصThe resultant sludge was extracted 5 times with mL of hexane
5. 5
   أخرىThis material was purified chromatographically (200 mesh Kieselgel 60, 2 % EtOAc 98% in hexane)

الإجراء التجريبي

The crude phenol 2i [4-(4-hydroxyphenyl)-benzonitrile] was dissolved in 250 mL of anh THF and added to a 500-mL 3-neck round-bottom flask and stirred at 25° C. Potassium tert-butoxide (0. 89 g, 8 mmol) was added to the solution, which turned yellow. Allyl bromide was added in excess (5.0 mL, 40 mmol) and the mixture was refluxed overnight. The THF and allyl bromide were removed by rotoevaporation. The resultant sludge was extracted 5 times with mL of hexane. This material was purified chromatographically (200 mesh Kieselgel 60, 2 % EtOAc 98% in hexane) to afford 1.0 g of white crystalline material (65%): mp 68°-69° C.; IR 3083, 3013, 2884, 2225, 1604, 1492, 1455, 1291, 1249, 1180, 995, 940, 824, 533 cm-1 ; 1H NMR δδ 7.6-7.8 (m, 4H), 7.4-7.5 (d, 2H), 6.9-7.0 (d, 2 H), 5.9-6.0 (m, 1 H), 5.2-5.4 (m, 2 H), 4.5 (d, 2 H); MS m/e 235 (M+), 220, 207, 166. Anal. Calcd for C14H11NO: C, 81.68; H, 5.56. Found C, 81.56; H, 5.68.

المصدر