Réaction #702667

Équation de réaction

ethyl salicylate

stearoyl chloride

triethylamine

→

title product

Rendement 95.2%

Ethyl 2-(octadecanoyloxy)benzoate

Rendement 95.2%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   TempératureAfter refluxing for 20 hours
2. 2
   AutreMost of the tetrahydrofuran was removed with a N2 stream during the cooling process
3. 3
   workup.ADDITIONThe residue was poured into ice/water (1500 ml)
4. 4
   Autrea white solid removed by filtration
5. 5
   LavageWashing the solid with water
6. 6
   Autredrying

Mode opératoire

To a cold (+5° C.) solution of ethyl salicylate (0.136 moles) and stearoyl chloride (0.136 moles) in tetrahydrofuran (200 ml) was added triethylamine (0.136 moles) dropwise over 25 min. After refluxing for 20 hours, the solution was cooled to room temperature. Most of the tetrahydrofuran was removed with a N2 stream during the cooling process. The residue was poured into ice/water (1500 ml), stirred for 1 hour, and a white solid removed by filtration. Washing the solid with water, followed by air drying gave 56 g of the title product, m.p. 50.5°-53.5° C.

Source