Carbon Dioxide → 7-hydroxy-5-methylcoumarin

HRID 990588노트

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HRID 990588 반응식
O.[CH3:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([CH:9]=1)[OH:8].C(O)(=O)[CH:12]([CH2:14][C:15](O)=O)[OH:13].S(=O)(O)[O-].[Na+].C(=O)=O>S(=O)(=O)(O)O>[OH:8][C:7]1[CH:6]=[C:5]2[C:4]([CH:15]=[CH:14][C:12](=[O:13])[O:10]2)=[C:3]([CH3:2])[CH:9]=1

참가 물질

6

반응물 4

HCID 280Carbon DioxideHCID 525Malic AcidHCID 3083941Resorcinol, 5-methyl-, monohydrateHCID 23665763Sodium Bisulfite

생성물 1

HCID 53556397-hydroxy-5-methylcoumarin수율 62%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
90 °C

실험 절차

5-methylresorcinol monohydrate (284 gm, 2.0 mol; Aldrich) was thoroughly mixed with malic acid (280 gm, 2.10 mol; Aldrich) and then placed in a reaction flask containing sulfuric acid (600 ml) and a trace of sodium bisulfite (1.0 gm; Aldrich). The reaction mixture was heated to 90° C. while being mechanically stirred until evolution of carbon dioxide subsided (about 5 hours). The resulting reddish-orange solution was poured into sufficient ice (with vigorous stirring) to make up 1 liter. The receiving flask was maintained at 0° C. by external cooling until the addition of the reaction mixture was complete. The resulting light-orange product that precipitated was collected by suction filtration then washed thoroughly with water. The crude product was air dried on the filter, then recrystallized twice from tetramethylene glycol (1800 ml) to give pure 7-hydroxy-5-methylcoumarin (H5MC,1) as product (220 gm, 62% yield; mp 252-255° C.).

후처리

  1. customplaced in a reaction flask
  2. custom(about 5 hours)
  3. additionThe resulting reddish-orange solution was poured into sufficient ice (with vigorous stirring)
  4. temperatureThe receiving flask was maintained at 0° C.
  5. temperatureby external cooling until the addition of the reaction mixture
  6. customThe resulting light-orange product that precipitated
  7. filtrationwas collected by suction filtration
  8. washthen washed thoroughly with water
  9. customdried on the filter
  10. customrecrystallized twice from tetramethylene glycol (1800 ml)

출처 및 근거

ORD 기록
ord-ea63121b44674486b04e5d70e8461d00
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06461567B1

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