Reaktion #689409

Reaktionsgleichung

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

potassium hydroxide

dimethyl formamide

Water

toluene

→

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto 45° C.
2. 2
   workup.STIRRINGIt was stirred for 3 hours
3. 3
   Sonstigewhile being kept at 45° C
4. 4
   Sonstigeseparated
5. 5
   Waschenthe 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
   Sonstigeobtained
8. 8
   workup.DISTILLATIONby distilling off toluene
9. 9
   Temperaturrefluxed for 2 hours
10. 10
    SonstigeThe residues obtained
11. 11
    workup.DISTILLATIONby distilling off ethanol
12. 12
    workup.ADDITIONwere poured into 5% hydrochloric acid (500 mL)
13. 13
    Sonstigeto obtain crystals
14. 14
    SonstigeThe crystals obtained by filtration
15. 15
    Sonstigewere recrystallized from a solvent mixture of ethanol and water

Vorschrift

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.

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