Ethyl 6-(4-chlorophenyl)-2,4,6-trioxohexanoate → 6-(4-Chlorophenyl)-4-oxo-4H-pyran-2-carboxylic acid

HRID 544172Notes

Reaction equation

HRID 544172 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]CC)=[O:14])=[CH:4][CH:3]=1>O1CCOCC1.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:20][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10](=[O:19])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

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

Product 1

HCID 128467126-(4-Chlorophenyl)-4-oxo-4H-pyran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of ethyl 6-(4-chlorophenyl)-2,4,6-trioxohexanoate (0.30 g) in dioxan (2 ml) and concentrated hydrochloric acid (2 ml) was heated on a steam bath for 2 hours. The pale solid which formed was recrystallised from ethanol to give the title product identical (mp, IR and NMR, and thin-layer chromatography) with the product described in Example 24.

Workup

  1. customThe pale solid which formed
  2. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-6a4e508b7eb8476b8f8c9d90ddfbc7de
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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