تفاعل #1175087

معادلة التفاعل

Benzyl chloride

6-hydroxy-α-methyl-2-naphthaleneacetic acid

sodium methoxide

→

white crystals

المردود 38.1%

α-Methyl-6-(phenylmethoxy)-2-naphthaleneacetic acid

المردود 38.1%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter 10 minutes the solvent is removed
2. 2
   درجة الحرارةThe reaction is then heated at 150° C. for 1 hour
3. 3
   أخرىThe solvent is then removed
4. 4
   أخرىthe residue is partitioned between water and methylene chloride
5. 5
   غسيلThe organic layer is washed with water
6. 6
   تجفيفdried over magnesium sulfate
7. 7
   أخرىevaporated to 11.5 g of crude product
8. 8
   استخلاصThis crude product is extracted with 100 ml hot hexane which

الإجراء التجريبي

To a solution of 6-hydroxy-α-methyl-2-naphthaleneacetic acid (6.48 g, 30 mmol) in methanol (100 ml) is added sodium methoxide (60 mm). After 10 minutes the solvent is removed and replaced with dimethylformamide (100 ml). Benzyl chloride (7.6 g, 60 mmol) is then added and the reaction mixture is stirred overnight at room temperature. The reaction is then heated at 150° C. for 1 hour. The solvent is then removed and the residue is partitioned between water and methylene chloride. The organic layer is washed with water, dried over magnesium sulfate and evaporated to 11.5 g of crude product. This crude product is extracted with 100 ml hot hexane which affords 3.5 g of white crystals. A final recrystallization from methanol affords 2.5 g of white crystals of the intermediate ethyl ester (21% yield, m.p. 76°-78° C.).

المصدر