Dimethylformamide → 4-(3-Ethyloxetane-3-ylmethoxy)benzoic acid

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence