Hydrochloric Acid → ethyl 5-hydroxy-4-oxo-4H-chromene-2-carboxylate

HRID 969595Notes

Reaction equation

HRID 969595 reaction equation
[Na].[CH3:2][C:3]([C:5]1[C:6]([OH:12])=[CH:7][CH:8]=[CH:9][C:10]=1[OH:11])=[O:4].[C:13](OCC)(=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl>C(O)C>[OH:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[C:3](=[O:4])[CH:2]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 696872',6'-DihydroxyacetophenoneHCID 5360545Sodium

Product 1

HCID 2801504ethyl 5-hydroxy-4-oxo-4H-chromene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.1 3.25 g of sodium are dissolved in portions in 300 ml of ethanol with stirring. A solution of 4.3 g of 2,6-dihydroxyacetophenone and 15.5 ml of diethyl oxalate in 25 ml of ethanol is subsequently added dropwise. The reaction mixture is subsequently heated at 80° for 3 hours. The mixture is cooled to room temperature, and 10 ml of 32% HCl are added dropwise. The mixture is heated at 90° for 30 minutes and cooled, and the solvent is removed. Conventional work-up gives 5.9 g of 5-hydroxy-2-ethoxycarbonyl-chromone (“AA”).

Workup

  1. temperatureThe reaction mixture is subsequently heated at 80° for 3 hours
  2. temperatureThe mixture is heated at 90° for 30 minutes
  3. temperaturecooled
  4. customthe solvent is removed

Sources & evidence

ORD record
ord-2c2e7d52385147d295a4f8ade8f2e4b4
Source dataset
uspto-grants-2007_12
Patent number
US07307100B2

Reaction notes

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