反応 #1175087

反応方程式

Benzyl chloride

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

sodium methoxide

→

white crystals

収率 38.1%

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

収率 38.1%

溶媒

methanol

反応条件

後処理

1. 1
   その他After 10 minutes the solvent is removed
2. 2
   温度The reaction is then heated at 150° C. for 1 hour
3. 3
   その他The solvent is then removed
4. 4
   その他the residue is partitioned between water and methylene chloride
5. 5
   洗浄The organic layer is washed with water
6. 6
   乾燥dried over magnesium sulfate
7. 7
   その他evaporated to 11.5 g of crude product
8. 8
   抽出This crude product is extracted with 100 ml hot hexane which

実験手順

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.).

出典