تفاعل #83879

معادلة التفاعل

sodium borohydride

1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone

sodium borohydride

→

4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol

المردود 55.0%

المذيبات

ethanol tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONAfter total addition
3. 3
   أخرىthe ice bath was removed
4. 4
   workup.STIRRINGAfter stirring at ambient temperature for one hour
5. 5
   أخرىthe solvent was removed in vacuo
6. 6
   workup.ADDITIONThe resultant solid residue was diluted with water (100 ml)
7. 7
   workup.WAITleft overnight
8. 8
   أخرىThe product was isolated by vacuum filtration
9. 9
   أخرىyielding 3.8 g
10. 10
    أخرىTwo consecutive recrystallizations from toluene

الإجراء التجريبي

To a flask charged with sodium borohydride (1.5 g, 39.4 mmol) under nitrogen and chilled to 10° C. was added, slowly, a solution of 1-[4-(3-chloropropoxy)-3-hydroxyphenyl]ethanone (6.0 g, 26.2 mmol) dissolved in ethanol-tetrahydrofuran (120 ml, 2:1). After total addition, the ice bath was removed and the reaction was stirred at ambient temperature for 3 hours. An additional amount of sodium borohydride (0.2 g, 5.3 mmol) was carefully added. After stirring at ambient temperature for one hour, the solvent was removed in vacuo. The resultant solid residue was diluted with water (100 ml) and left overnight. The product was isolated by vacuum filtration yielding 3.8 g. Two consecutive recrystallizations from toluene provided 3.3 g (55%) of 4-(3-chloropropoxy)-3-hydroxy-α-methylbenzene methanol as a light brown solid, m.p.=107°-109° C.

المصدر