Reaction #577205

Reaction equation

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

ethyl hydroxybiphenylcarboxylate

potassium hydroxide

ethanol

→

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

Yield 51.7%

Solvents

toluene

Water

Conditions

Workup

1. 1
   Otherto 45° C.
2. 2
   Temperaturerefluxed for 2 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.ADDITION20 g of sodium hydroxide, 500 mL of ethanol and 100 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 ethanol

Procedure

12 g of ethyl hydroxybiphenylcarboxylate and 15 g of potassium hydroxide were added to 100 mL of ethanol, and stirred at 60° C. for 1 hour. After decreasing the temperature to 45° C., 15 g of 3-((tosyloxy)methyl)-3-ethyloxetane was added dropwise thereto, and then refluxed for 2 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. 20 g of sodium hydroxide, 500 mL of ethanol and 100 mL of water were added to the resulting residue, and refluxed for 2 hours. A residue obtained by distilling ethanol off was put in 300 mL of 5% hydrochloric acid to obtain crystals. The crystals thus obtained by filtering were recrystallized from ethanol to obtain 8 g of 4-(3-ethyloxetane-3-ylmethoxy)biphenylcarboxylic acid (OX2), which had a melting point of 222 to 225° C.

Source