تفاعل #55650

معادلة التفاعل

3-[2-(4-methoxyphenyl)ethyl]-glutaric acid

ethanethiol

→

title compound

المردود 88.0%

3-[2-(4-Hydroxyphenyl)ethyl]glutaric acid

المردود 88.0%

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىresults
2. 2
   درجة الحرارةthe mixture is heated
3. 3
   workup.STIRRINGwith stirring in a bath at 165° C. for 6.0 hours
4. 4
   أخرىThe mixture is then evaporated to dryness in vacuo
5. 5
   workup.DISSOLUTIONthe resulting residue is dissolved in water (50 ml)
6. 6
   استخلاصextracted with ether (two 50 ml portions)
7. 7
   استخلاصthe ether extract
8. 8
   استخلاصextracted with ethyl acetate
9. 9
   غسيلThe ethyl acetate solution is washed with brine
10. 10
    تجفيفdried with anhydrous magnesium sulfate
11. 11
    أخرىevaporated to a residue
12. 12
    أخرىCrystallization of this from chloroform-hexane

الإجراء التجريبي

To a suspension of 57% sodium hydride-paraffin (2.2 g) in dry dimethylformamide (70 ml) in an atmosphere of nitrogen is slowly added ethanethiol (4.0 ml). The mixture is stirred at room temperature until a clear solution results. To this solution is added a solution of 3-[2-(4-methoxyphenyl)ethyl]-glutaric acid (1.2 g) in dry dimethylformamide (10 ml) and the mixture is heated with stirring in a bath at 165° C. for 6.0 hours. The mixture is then evaporated to dryness in vacuo and the resulting residue is dissolved in water (50 ml), extracted with ether (two 50 ml portions) and the ether extract is discarded. The aqueous solution is acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried with anhydrous magnesium sulfate, and evaporated to a residue. Crystallization of this from chloroform-hexane affords 1.0 g of the title compound, melting point 142°-144° C.

المصدر