Malic Acid → 7-Hydroxy-8-methyl coumarin

HRID 564880

Reaction equation

HRID 564880 reaction equation
[CH3:1][C:2]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4].C(O)(=O)[CH:11]([CH2:13][C:14](O)=O)[OH:12]>S(=O)(=O)(O)O>[OH:4][C:3]1[C:2]([CH3:1])=[C:8]2[C:7]([CH:14]=[CH:13][C:11](=[O:12])[O:9]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 525Malic AcidHCID 118432-Methylresorcinol

Product 1

HCID 53809787-Hydroxy-8-methyl coumarinYield 20.64%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
80 °C

Procedure

2-methyl resorcinol (0.161 mmol, 20.024 g) and malic acid (0.165 mmol, 22.129 g) were dissolved in concentrated sulfuric acid. The reaction mixture was stirred at 80° C. for 24 h. The resulting solution was then poured over crushed ice, and the precipitate was collected by vacuum filtration. The precipitate was then washed with 5% NaHCO3 and again collected by vacuum filtration yielding an orange-yellow solid in a 20.64% yield.

Workup

  1. additionThe resulting solution was then poured
  2. customover crushed ice
  3. filtrationthe precipitate was collected by vacuum filtration
  4. washThe precipitate was then washed with 5% NaHCO3
  5. filtrationagain collected by vacuum filtration
  6. customyielding an orange-yellow solid in a 20.64% yield

Sources & evidence

ORD record
ord-99dfb82c3f9d41f2b7d1210e9fa151d3
Source dataset
uspto-grants-2001_01
Patent number
US06169109A

Linked notes

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