Carbon Dioxide → 7-hydroxy-5-methylcoumarin

HRID 1588215ノート

反応式

HRID 1588215 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 53556397-hydroxy-5-methylcoumarin収率 62%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
90 °C

実験手順

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.).

後処理

  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)

出典と根拠

ORDレコード
ord-686277d753f141018e41de6781254259
出典データセット
uspto-grants-1993_06
特許番号
US05221608

反応ノート

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