Reacción #833529

Ecuación de reacción

3-[(tosyloxy)methyl]-3-ethyloxetane

potassium hydroxide

dimethyl formamide

Water

toluene

→

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

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto 45° C.
2. 2
   workup.STIRRINGIt was stirred for 3 hours
3. 3
   Otrowhile being kept at 45° C
4. 4
   Otroseparated
5. 5
   Lavadothe toluene layer was washed with 3% hydrochloric acid
6. 6
   workup.ADDITIONSodium hydroxide (50 g), ethanol (500 mL) and water (200 mL) were added to residues
7. 7
   Otroobtained
8. 8
   workup.DISTILLATIONby distilling off toluene
9. 9
   Temperaturarefluxed for 2 hours
10. 10
    OtroThe residues obtained
11. 11
    workup.DISTILLATIONby distilling off ethanol
12. 12
    workup.ADDITIONwere poured into 5% hydrochloric acid (500 mL)
13. 13
    Otroto obtain crystals
14. 14
    OtroThe crystals obtained by filtration
15. 15
    Otrowere recrystallized from a solvent mixture of ethanol and water

Procedimiento

A mixture of ethyl hydroxyl benzoate (50 g), potassium hydroxide (21 g), and dimethyl formamide (400 mL) was stirred at 70° C. for one hour. After lowering the temperature to 45° C., 3-[(tosyloxy)methyl]-3-ethyloxetane (100 g) was dropped to the reaction mixture. It was stirred for 3 hours while being kept at 45° C. Water and toluene were added and separated, and the toluene layer was washed with 3% hydrochloric acid, an aqueous saturated solution of sodium hydrogen carbonate and water. Sodium hydroxide (50 g), ethanol (500 mL) and water (200 mL) were added to residues obtained by distilling off toluene and refluxed for 2 hours. The residues obtained by distilling off ethanol were poured into 5% hydrochloric acid (500 mL) to obtain crystals. The crystals obtained by filtration were recrystallized from a solvent mixture of ethanol and water to obtain 4-(3-ethyloxetane-3-ylmethoxy)benzoic acid (OX5: 60 g). Melting point: 127.5° C.

Fuente