Malic Acid → 7-hydroxy-5-methylcoumarin

HRID 1106265ノート

反応式

HRID 1106265 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH:8]=1)[OH:7].C(O)(=O)[CH:11]([CH2:13][C:14](O)=O)[OH:12].OS(O)(=O)=O>O>[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]2[C:8]=1[CH:14]=[CH:13][C:11](=[O:12])[O:7]2

参加物

5

反応物 3

HCID 525Malic AcidHCID 1118Sulfuric AcidHCID 10436Orcinol

生成物 1

HCID 53556397-hydroxy-5-methylcoumarin収率 43.9%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 5-methylresorcin (25.0 g), malic acid (26.0 g) and conc.H2SO4 (55 ml) was gently heated with the gaseous development almost ceased. The reaction mixture was then poured with vigorous stirring into a mixture of water and ice (700 ml), and stirred until the gummy mass initially formed was completely dispersed. The precipitate was collected by filtration, washed with water and crystallized twice (Me2CO) producing 5-methyl-7-hydroxycoumarin (I; 15 g; m.p. 256° C.) ##STR4## free from the isomer 5-hydroxy-7-methylcoumarin (II). ##STR5##

後処理

  1. additionThe reaction mixture was then poured
  2. custominitially formed
  3. additionwas completely dispersed
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customcrystallized twice (Me2CO)

出典と根拠

ORDレコード
ord-cd5dce67e5074ffbb8fbe6dddbd51add
出典データセット
uspto-grants-1982_01
特許番号
US04312883

反応ノート

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