Hydrochloric Acid → 2-Ethyl-7-hydroxy-4H-1-benzopyran-4-one

HRID 1681121Notes

Reaction equation

HRID 1681121 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:17]=[C:16]([O:18]C(=O)CC)[CH:15]=[CH:14][C:6]=2[C:7](=[O:13])[C:8]=1C(=O)CC)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].Cl.CCOCC.C(Cl)Cl>O>[CH2:1]([C:3]1[O:4][C:5]2[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:6]=2[C:7](=[O:13])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 15171688HCID 15171688, compoundHCID 21881112Ethyl ether methylene chloride

Product 1

HCID 151716892-Ethyl-7-hydroxy-4H-1-benzopyran-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 6.5 g (21.5.10-3 mol) of 2-ethyl-7-(1-oxopropoxy)-3-(1-oxopropyl)-4H-1benzopyran-4-one and 5 g (47.403 mol) of sodium carbonate in 65 ml of water is kept at a temperature of 150° C. for 9 hours. The reaction mixture is hydrolyzed with a 1N solution of hydrochloric acid. The product is extracted with ethyl acetate. After purification by chromatography on silica gel using an ether/methylene chloride mixture (1/2 v/v) as the eluent, 2.45 g (yield: 61%) of the expected product are obtained.

Workup

  1. extractionThe product is extracted with ethyl acetate

Sources & evidence

ORD record
ord-c1cb9593a6044e61811a32f469537053
Source dataset
uspto-grants-1992_12
Patent number
US05169838

Reaction notes

Loading…