تفاعل #10575

معادلة التفاعل

4

4-Tetrahydropyranyloxy-4′-trifluormethyltolan

CH2Cl2

TsOH

→

crystal

5-Hydroxy-4′-trifluoromethyltolan

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   أخرىwas removed by rotary evaporation
2. 2
   workup.DISSOLUTIONthe residue was dissolved in EtOAc
3. 3
   ترشيحfiltered through silica gel
4. 4
   أخرىThe solvent was removed
5. 5
   أخرىthe solid was recrystallized from solvents of ethyl acetate and hexane (1:5)

الإجراء التجريبي

Coumpound 4 (13.84 g, 40 mmol), CH2Cl2 (75 ml) and MeOH (125 ml) were placed in a 250 ml round bottomed flask, then TsOH (0.4 g, 0.4 mmol) was added. The reaction mixture was stirred at 30° C. for 1 hour. When the reaction was finished (TLC shows no starting material remaining), the solvent was removed by rotary evaporation and the residue was dissolved in EtOAc and filtered through silica gel. The solvent was removed and the solid was recrystallized from solvents of ethyl acetate and hexane (1:5) to give a pale yellow crystal 9.5 g (90%), mp 131–132° C., δH(CDCl3; 300 MHz): 7.59(s, 4H, Ar—H), 7.44(d, J=8.7, 2H, Ar—H), 6.82(d, J−8.7, 2H, Ar—H), 5.16(s, 1H, OH).

المصدر