Reaction #833526

Reaction equation

3-[(6-bromohexyloxy)methyl]-3-methyloxetane

ethyl 4-hydroxybenzoate

potassium carbonate

dimethyl formamide

→

ethyl 4-[6-(2-methyloxetane-3-ylmetoxy)hexyloxy)benzoate

Yield 80.6%

Solvents

Water

Conditions

Workup

1. 1
   Otherto terminate
2. 2
   Otherthe reaction
3. 3
   Extractionafter extraction with ethyl acetate
4. 4
   Extractionthe liquid extract
5. 5
   Washwas washed with an aqueous solution of 2N-sodium hydroxide and water successively
6. 6
   Dryingthe organic layer was dried over anhydrous magnesium sulfate
7. 7
   OtherThe residues obtained
8. 8
   workup.DISTILLATIONby distilling off the solvent
9. 9
   Otherwere purified on silica gel chromatography (toluene/ethyl acetate=8/2)

Procedure

A mixture of 3-[(6-bromohexyloxy)methyl]-3-methyloxetane (84 g), ethyl 4-hydroxybenzoate (50 g), potassium carbonate (50 g) and dimethyl formamide (600 mL) was stirred at 90° C. for 4 hours. Water was added to the reaction mixture to terminate the reaction and, after extraction with ethyl acetate, the liquid extract was washed with an aqueous solution of 2N-sodium hydroxide and water successively, and the organic layer was dried over anhydrous magnesium sulfate. The residues obtained by distilling off the solvent were purified on silica gel chromatography (toluene/ethyl acetate=8/2), to obtain ethyl 4-[6-(2-methyloxetane-3-ylmetoxy)hexyloxy)benzoate (85 g).

Source