Hydrochloric Acid → 4-Hydroxy-7-methylcoumarin

HRID 2422481노트

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HRID 2422481 반응식
[H-].[Na+].[OH:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11](=[O:13])[CH3:12].[C:14](=O)(OCC)[O:15]CC.Cl>C1(C)C=CC=CC=1>[OH:13][C:11]1[C:5]2[C:4](=[CH:9][C:8]([CH3:10])=[CH:7][CH:6]=2)[O:3][C:14](=[O:15])[CH:12]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 813382'-Hydroxy-4'-methylacetophenone

생성물 1

HCID 546853074-Hydroxy-7-methylcoumarin

시약·촉매·용매 1

HCID 1140Toluene용매3회

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온도
80 °C

실험 절차

To a mechanically stirred suspension of sodium hydride (60% in oil, 30 g, 749 mmol) in toluene (400 mL), heated at 80° C., a solution of the commercially available 2′-hydroxy-4′-methylacetophenone (50 g, 0.333 mmol) in 150 mL of toluene was added dropwise over 1 h. After complete addition, the mixture was stirred 15 min and a solution of diethyl carbonate (81 mL, 666 mmol) in toluene (500 mL) was added dropwise over 1 h. The reaction mixture was then stirred overnight at reflux. After cooling, the reaction mixture was poured into 800 mL of 2N HCl. The precipitate formed was collected by filtration, co-evaporated twice with toluene and dried under high vacuum at 55° C. 1H NMR (400 MHz, acetone-d6): 11.1 (bs, 1H), 7.76 (d, 1H), 7.18 (d, 1H), 7.14 (s, 1H), 5.60 (s, 1H), 2.47 (s, 3H).

후처리

  1. additionAfter complete addition
  2. stirringThe reaction mixture was then stirred overnight
  3. temperatureat reflux
  4. temperatureAfter cooling
  5. customThe precipitate formed
  6. filtrationwas collected by filtration
  7. customdried under high vacuum at 55° C

출처 및 근거

ORD 기록
ord-51e75555139f4c4e9129d87f44530ea9
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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