Reacción #4688

Ecuación de reacción

1-naphthol

sodium hydride

bromomalonic acid diethyl ester

→

α-naphthoxymalonic acid diethyl ester

Disolventes

DMF

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThe reaction mixture is further stirred for 16 hours at room temperature
2. 2
   Concentraciónconcentrated by evaporation in a high vacuum
3. 3
   workup.DISSOLUTIONThe residue is dissolved in ethyl acetate
4. 4
   Lavadowashed with 2N sodium hydroxide solution, water and brine
5. 5
   Secadodried over sodium sulphate
6. 6
   Concentraciónconcentrated by evaporation
7. 7
   workup.DISTILLATIONThe residue is distilled at 145°-170°/2.6 Pa

Procedimiento

A solution of 25 g of 1-naphthol in 50 ml of DMF is slowly added dropwise to a solution of 7.6 g of sodium hydride dispersion in 300 ml of DMF. The suspension is stirred for 30 minutes and subsequently 41.5 g of bromomalonic acid diethyl ester in 50 ml of DMF are added dropwise. The reaction mixture is further stirred for 16 hours at room temperature and then concentrated by evaporation in a high vacuum. The residue is dissolved in ethyl acetate and washed with 2N sodium hydroxide solution, water and brine, dried over sodium sulphate and concentrated by evaporation. The residue is distilled at 145°-170°/2.6 Pa and yields α-naphthoxymalonic acid diethyl ester in the form of an orange-coloured oil.

Fuente