반응 #95936

반응 방정식

1-acetyl-3,4-dihydro-anthraquinone

1-hydroxy-3,4-dihydroanthraquinone

acetic anhydride

1-acetyl-3,4-dihydroanthraquinone

N-bromosuccinimide

→

1-hydroxy-3(carboxymethyl)-3,4-dihydroanthraquinone

용매

water

carbon tetrachloride

pyridine

반응 조건

후처리

1. 1
   기타It is collected
2. 2
   세척washed
3. 3
   기타dried at 80° C.
4. 4
   온도under reflux for 2 hours
5. 5
   기타1-acetyl-3-bromo-3,4-dihydroanthraquinone is collected
6. 6
   workup.DISSOLUTIONdissolved in acetone
7. 7
   workup.ADDITIONtreated with ethyl 2-bromoacetate and excess copper powder
8. 8
   온도under reflux, for 2 hours
9. 9
   기타The ethyl ester of 1-acetoxy-3(carboxymethyl)-3,4-dihydroanthraquinone is collected

실험 절차

1-hydroxy-3,4-dihydroanthraquinone is reacted with 2 moles of acetic anhydride in pyridine for 15 hours. The mixture is poured into water, when 1-acetyl-3,4-dihydro-anthraquinone separates. It is collected, washed and dried at 80° C. and 2 Pa absolute (15 torr). The 1-acetyl-3,4-dihydroanthraquinone is reacted with 2 moles of N-bromosuccinimide while suspended in boiling carbon tetrachloride under reflux for 2 hours. 1-acetyl-3-bromo-3,4-dihydroanthraquinone is collected, dissolved in acetone and treated with ethyl 2-bromoacetate and excess copper powder, under reflux, for 2 hours. The ethyl ester of 1-acetoxy-3(carboxymethyl)-3,4-dihydroanthraquinone is collected and hydrolysed by standing overnight in N sodium hydroxide solution under nitrogen. The free acid, 1-hydroxy-3(carboxymethyl)-3,4-dihydroanthraquinone is then obtained on acidification.

출처