Hydrochloric Acid → ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

HRID 1193664Notes

Reaction equation

HRID 1193664 reaction equation
[Na].[CH3:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:12])=[CH:9][C:10]=1[OH:11])=[O:4].[CH2:13]([O:15][C:16](=[O:22])[C:17](OCC)=O)[CH3:14].Cl>C(O)C.C(OCC)C.O>[CH2:13]([O:15][C:16]([C:17]1[O:11][C:10]2[CH:9]=[C:8]([OH:12])[CH:7]=[CH:6][C:5]=2[C:3](=[O:4])[CH:2]=1)=[O:22])[CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 69902',4'-DihydroxyacetophenoneHCID 7268Diethyl OxalateHCID 5360545Sodium

Product 1

HCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a warm, stirred solution of 18.4 g (0.8 mole) of sodium metal in 250 ml of absolute ethanol was added dropwise a solution of 30.4 g (0.2 mole) of 2,4-dihydroxyacetophenone and 58.5 g (0.4 mole) of diethyloxalate in 50 ml of absolute ethanol and 50 ml of absolute ethyl ether over a 30 min period. The mixture was heated at reflux for 4 hr and then poured into a solution of 200 ml of concentrated hydrochloric acid and 1.8 liter of water. The mixture was extracted with two 500 ml portions of ethyl ether and the combined extracts were concentrated under reduced pressure to give a solid residue.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 hr
  3. extractionThe mixture was extracted with two 500 ml portions of ethyl ether
  4. concentrationthe combined extracts were concentrated under reduced pressure
  5. customto give a solid residue

Sources & evidence

ORD record
ord-a9a10eaede0b4ae5bddef62a993eb78f
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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