Hydrochloric Acid → 7-Hydroxycoumarin-4-propionic acid

HRID 363143노트

반응식

HRID 363143 반응식
C([O:3][C:4](=[O:15])[CH2:5][C:6](=O)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])C.[C:16]1(C=C[CH:21]=[C:19](O)[CH:18]=1)[OH:17].Cl>C(O)C>[OH:17][C:16]1[CH:13]=[C:12]2[C:21]([C:7]([CH2:6][CH2:5][C:4]([OH:3])=[O:15])=[CH:8][C:9](=[O:10])[O:11]2)=[CH:19][CH:18]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric Acid2회HCID 5054ResorcinolHCID 81576Diethyl 3-oxoadipate2회

생성물 1

HCID 152907807-Hydroxycoumarin-4-propionic acid수율 73%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 3-oxohexane-1,6-dioic acid diethyl ester (78.88 g), resorcinol (40.19 g) and ethanol (1 L) was saturated with hydrogen chloride gas during two hours at 0° C., tightly stoppered, let stand at room temperature over the weekend, shown by thin layer chromatography to contain unreacted 3-oxohexane-1,6-dioic acid diethyl ester, saturated again with hydrogen chloride gas during 45 minutes at 0° C., and let stand overnight at room temperature. Although thin layer chromatography still showed that the reaction was incomplete, the solution was partially (800 mL) stripped of volatiles and poured into ice-water. The resulting solid was collected by filtration and ethanol (300 mL) and aqueous sodium hydroxide solution (2.5N, 350 mL) were added. The mixture was stirred at room temperature and, when the reaction was complete, poured into hydrochloric acid (2N, 500 mL). A suspension of the resulting solid in methanol (300 mL) was stirred for 15 minutes at room temperature, cooled on ice and filtered. The resulting solid was washed with ether and dried affording 3-(7-hydroxy-4-coumarinyl)propionic acid (62.4 g, 73% yield).

후처리

  1. customlet stand at room temperature over the weekend
  2. filtrationThe resulting solid was collected by filtration and ethanol (300 mL) and aqueous sodium hydroxide solution (2.5N, 350 mL)
  3. additionwere added
  4. additionpoured into hydrochloric acid (2N, 500 mL)
  5. additionA suspension of the resulting solid in methanol (300 mL)
  6. stirringwas stirred for 15 minutes at room temperature
  7. temperaturecooled on ice
  8. filtrationfiltered
  9. washThe resulting solid was washed with ether
  10. customdried

출처 및 근거

ORD 기록
ord-54526fc7d70649cf8f9e7193cc17358b
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872207

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