تفاعل #76286

معادلة التفاعل

boron trifluoride diethyl etherate

4-bromo-2-(3,5-dimethoxyphenoxy)benzoic acid

4-Bromo-2-(3,5-dimethoxyphenoxy)benzoic Acid

sodium borohydride

→

alcohol

المردود 64.5%

4-Bromo-2-(3,5-dimethoxyphenoxy)benzyl Alcohol

المردود 64.5%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe resulting solution was extracted with ethyl acetate
2. 2
   غسيلthe extract was washed with a saturated sodium chloride aqueous solution three times
3. 3
   تجفيفAfter drying with anhydrous magnesium sulfate
4. 4
   أخرىthe solvent was removed under reduced pressure
5. 5
   أخرىThe residue was recrystallized from benzene-diisopropyl ether

الإجراء التجريبي

To a solution of 75.4 g (F.W. 353.168, 213 mmol) of 4-bromo-2-(3,5-dimethoxyphenoxy)benzoic acid (22) in 300 mL of tetrahydrofuran was added 8.9 g (F.W. 37.83, 235 mmol) of sodium borohydride portionwise at room temperature and then, 31 mL (F.W. 141.93, d=1.154, 252 mmol) of boron trifluoride diethyl etherate was added thereto dropwise. The resulting solution was stirred at room temperature for one hour. To this reaction solution was added 200 mL of ice water slowly. The resulting solution was extracted with ethyl acetate and the extract was washed with a saturated sodium chloride aqueous solution three times. After drying with anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The residue was recrystallized from benzene-diisopropyl ether to obtain 46.6 g (64%) of alcohol (23). (TLC; ethyl acetate:hexane=1:4).

المصدر