Réaction #833529

Équation de réaction

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

potassium hydroxide

dimethyl formamide

Water

toluene

→

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

Conditions de réaction

Traitement

1. 1
   Autreto 45° C.
2. 2
   workup.STIRRINGIt was stirred for 3 hours
3. 3
   Autrewhile being kept at 45° C
4. 4
   Autreseparated
5. 5
   Lavagethe 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
   Autreobtained
8. 8
   workup.DISTILLATIONby distilling off toluene
9. 9
   Températurerefluxed for 2 hours
10. 10
    AutreThe residues obtained
11. 11
    workup.DISTILLATIONby distilling off ethanol
12. 12
    workup.ADDITIONwere poured into 5% hydrochloric acid (500 mL)
13. 13
    Autreto obtain crystals
14. 14
    AutreThe crystals obtained by filtration
15. 15
    Autrewere recrystallized from a solvent mixture of ethanol and water

Mode opératoire

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.

Source