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

HRID 1709840Notes

Reaction equation

HRID 1709840 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-63b1824ec2b64eb09451c459f8878ff9
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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