Malic Acid → Coumalic acid

HRID 904286Notes

Reaction equation

HRID 904286 reaction equation
C(O)(=O)[CH:2]([CH2:4][C:5]([OH:7])=[O:6])[OH:3].S(=O)(=O)(O)O.OS(O)(=O)=O.O=S(=O)=O>O>[CH:5]1[C:4]([C:5]([OH:7])=[O:6])=[CH:2][O:3][C:2](=[O:3])[CH:4]=1

Participants

5

Reactant 3

HCID 525Malic AcidHCID 1118Sulfuric AcidHCID 24681Fuming sulfuric acid

Product 1

HCID 68141Coumalic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 200 g of malic acid was added 175 cc of concentrated sulfuric acid and 1 g of 65% oleum. The mixture was heated to 100° C. for two hours, cooled to 30° C. and diluted with 300 cc of water. The reaction mixture was cooled to 25° C. and filtered to give coumalic acid.

Workup

  1. temperaturecooled to 30° C.
  2. temperatureThe reaction mixture was cooled to 25° C.
  3. filtrationfiltered

Sources & evidence

ORD record
ord-64ac0670244941ec9c5226455a41534c
Source dataset
uspto-grants-1980_10
Patent number
US04230864

Reaction notes

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