Reaction #2981

Reaction equation

triethylamine

mesyl chloride

2-(7-methoxy-1-naphthyl)ethanol

→

2-(7-METHOXY-1-NAPHTHYL)ETHYL MESYLATE

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.WAITThe mixture is left
2. 2
   workup.STIRRINGstirring for 30 minutes
3. 3
   ExtractionThe aqueous phase is extracted with 3 times 50 cm3 of dichloromethane
4. 4
   Washthe organic phase is washed with 3 times 20 cm3 of 1N hydrochloric acid solution
5. 5
   Dryingwith water, dried over potassium carbonate
6. 6
   Otherevaporated
7. 7
   OtherThe oily residue is recrystallized

Procedure

In a 250-cm3 flask, 4 g of 2-(7-methoxy-1-naphthyl)ethanol are dissolved in 100 cm3 of dichloromethane, and 3.3 cm3 of triethylamine are added. The mixture is cooled in an ice bath at -10° C. and 2.75 g of mesyl chloride are then added dropwise and with stirring. The mixture is left stirring for 30 minutes. The aqueous phase is extracted with 3 times 50 cm3 of dichloromethane, and the organic phase is washed with 3 times 20 cm3 of 1N hydrochloric acid solution and then with water, dried over potassium carbonate and evaporated. The oily residue is recrystallized.

Source