Reaction #577204

Reaction equation

3-((tosyloxy)methyl)-3-ethyloxetane

ethyl hydroxybenzoate

potassium hydroxide

dimethylformamide

→

4-(3-ethyloxetane-3-ylmethoxy)benzoic acid

Yield 84.4%

Solvents

toluene

Water

Conditions

Workup

1. 1
   Otherto 45° C.
2. 2
   workup.STIRRINGstirred at 45° C. for 3 hours
3. 3
   Otherthe toluene layer was separated
4. 4
   WashThe toluene layer was washed with 3% hydrochloric acid
5. 5
   workup.DISTILLATIONa saturated sodium carbonate solution and water, and then toluene was distilled off
6. 6
   workup.ADDITION50 g of sodium hydroxide, 500 mL of ethanol and 200 mL of water were added to the resulting residue
7. 7
   Temperaturerefluxed for 2 hours
8. 8
   OtherA residue obtained
9. 9
   workup.DISTILLATIONby distilling ethanol
10. 10
    Otherto obtain crystals
11. 11
    OtherThe crystals thus obtained
12. 12
    Filtrationby filtering
13. 13
    Otherwere recrystallized from a mixed solvent of ethanol and water

Procedure

50 g of ethyl hydroxybenzoate and 21 g of potassium hydroxide were added to 400 mL of dimethylformamide, and stirred at 70° C. for 1 hour. After decreasing the temperature to 45° C., 100 g of 3-((tosyloxy)methyl)-3-ethyloxetane was added dropwise thereto, and then stirred at 45° C. for 3 hours. Water and toluene were added thereto, and the toluene layer was separated. The toluene layer was washed with 3% hydrochloric acid, a saturated sodium carbonate solution and water, and then toluene was distilled off. 50 g of sodium hydroxide, 500 mL of ethanol and 200 mL of water were added to the resulting residue, and refluxed for 2 hours. A residue obtained by distilling ethanol off was put in 500 mL of 5% hydrochloric acid to obtain crystals. The crystals thus obtained by filtering were recrystallized from a mixed solvent of ethanol and water to obtain 60 g of 4-(3-ethyloxetane-3-ylmethoxy)benzoic acid (OX1), which had a melting point of 127.5° C.

Source