Ethanol → Ethyl alpha-nitro-9H-xanthene-9-acetate

HRID 258187

반응식

HRID 258187 반응식
O[CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[N+:16]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17].[OH-].[K+].C(O)C>O>[N+:16]([CH:19]([CH:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:18])=[O:17]

참가 물질

6

반응물 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 69379Ethyl nitroacetateHCID 72861Xanthydrol

생성물 1

HCID 15290758Ethyl alpha-nitro-9H-xanthene-9-acetate

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

9-Hydroxyxanthene (9.9 g, 50 mmol) and ethyl nitroacetate (6.1 mL, 55 mol) are mixed and heated at 100° C. (oil bath) for 1.5 hours. After cooling, a waxy mixture is suspended in 40 mL of absolute alcohol and 40 mL of 1.25 M of ethanolic potassium hydroxide solution is added. The solution is stirred for 45 minutes at room temperature and ethanol is stripped off. The remaining solid is suspended in water and extracted with diethyl ether. The aqueous portion is acidified with 85% phosphoric acid to pH 2 to 3 to give a white suspension which is cooled overnight. The precipitate is collected by filtration and dried in a vacuum oven at 50° C. This gives 9.18 g of the title compound as a white solid; mp 89°-91° C.

후처리

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. customto give a white suspension which
  4. temperatureis cooled overnight
  5. filtrationThe precipitate is collected by filtration
  6. customdried in a vacuum oven at 50° C

출처 및 근거

ORD 기록
ord-0ae9fb3e0f2140cf8791a86601f25eb2
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264577

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