Malic Acid → 7-hydroxy-5-methylcoumarin

HRID 1106265노트

반응식

HRID 1106265 반응식
[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

참가 물질

5

반응물 3

HCID 525Malic AcidHCID 1118Sulfuric AcidHCID 10436Orcinol

생성물 1

HCID 53556397-hydroxy-5-methylcoumarin수율 43.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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##

후처리

  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)

출처 및 근거

ORD 기록
ord-cd5dce67e5074ffbb8fbe6dddbd51add
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04312883

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