Reaction #66040

Reaction equation

1-docosanyl methanesulfonate

tetraethylene glycol

t-butoxypotassium

→

white crystal

tetraethylene glycol mono-1-docosanyl ether

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperatureafter cooling
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   Filtration22.2 g of an insoluble matter was filtered
4. 4
   ExtractionAn ethyl acetate phase was extracted
5. 5
   Otherseparated from the filtrate
6. 6
   Concentrationafter concentration under reduced pressure, 0.5 L of acetonitrile
7. 7
   workup.ADDITIONwas added
8. 8
   workup.STIRRINGthe mixture was stirred under ice cooling for one hour
9. 9
   FiltrationThe reaction mixture was filtered under reduced pressure
10. 10
    Washwashed with 0.2 L of cold acetonitrile

Procedure

80.4 g of 1-docosanyl methanesulfonate was added to 207 mL of tetraethylene glycol, and the mixture was heated at 110° C. 40.0 g of t-butoxypotassium was gradually added over 2 hours. The mixture was further stirred for 3 hours, and after cooling, the reaction mixture was poured into 3 L of ice water, to which was then added 2 L of ethyl acetate, the mixture was stirred, and 22.2 g of an insoluble matter was filtered. An ethyl acetate phase was extracted and separated from the filtrate, after concentration under reduced pressure, 0.5 L of acetonitrile was added, and the mixture was stirred under ice cooling for one hour. The reaction mixture was filtered under reduced pressure and washed with 0.2 L of cold acetonitrile to obtain 81.6 g of a white crystal.

Source