Ethyl 6-(4-chlorophenyl)-2,4,6-trioxohexanoate → Ethyl 6-(4-chlorophenyl)-4-oxo-4H-pyran-2-carboxylate

HRID 544171Notes

Reaction equation

HRID 544171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10](=[O:19])[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:20][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10](=[O:19])[CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 15578432Ethyl 6-(4-chlorophenyl)-2,4,6-trioxohexanoate

Product 1

HCID 550407Ethyl 6-(4-chlorophenyl)-4-oxo-4H-pyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of ethyl 6-(4-chlorophenyl)-2,4,6-trioxohexanoate (0.26 g) in cold concentrated sulphuric acid (3 ml) was stirred for 3 hours at 0°-5° C. then poured on to ice (10 g). The solid product was recrystallised from ethanol-water to give the title product identical (mp, IR and NMR, and thin-layer chromatography) with the product described in Example 12.

Workup

  1. customThe solid product was recrystallised from ethanol-water

Sources & evidence

ORD record
ord-bf6c4fd517714ba5b2fc39815d0f3a7f
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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