Reacción #335360

Ecuación de reacción

Benzyl chloride

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

sodium methoxide

→

white crystals

Rendimiento 38.1%

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

Rendimiento 38.1%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter 10 minutes the solvent is removed
2. 2
   TemperaturaThe reaction is then heated at 150° C. for 1 hour
3. 3
   OtroThe solvent is then removed
4. 4
   Otrothe residue is partitioned between water and methylene chloride
5. 5
   LavadoThe organic layer is washed with water
6. 6
   Secadodried over magnesium sulfate
7. 7
   Otroevaporated to 11.5 g of crude product
8. 8
   ExtracciónThis crude product is extracted with 100 ml hot hexane which

Procedimiento

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 mmol). 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 ether ester (21% yield, m.p. 76°-78° C.).

Fuente