Quinone → HCID 20059334, compound

HRID 1085929Notes

Reaction equation

HRID 1085929 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8]O[C:6](=O)[CH:5]=1)[CH3:2].[C:16]1(=[O:23])C=[CH:20][C:19](=[O:22])[CH:18]=[CH:17]1>C1C(Cl)=CC=C(Cl)C=1.O=[Mn]=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:20](=[CH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:19](=[O:22])[CH:18]=[CH:17][C:16]2=[O:23])[CH3:2]

Participants

5

Reactant 2

HCID 4650QuinoneHCID 14591481HCID 14591481, compound

Product 1

HCID 20059334HCID 20059334, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 46851,4-DichlorobenzeneSolvent

Procedure

0.42 g (0.002 mol) of ethyl 4-ethoxy-2-oxo-2H-pyran-5-carboxylate, 1.08 g (0.01 mol) of 1,4-benzoquinone and 0.54 g (0.0062 mol) of MnO2 in 4.8 ml of dichlorobenzene are heated at 180° C. for 12 hours. The resulting reaction mixture is chromatographed over a column of 30 g of silica gel 60 (mobile phase 99:1 CH2Cl2 /acetone, 0.3 bar excess pressure). This gives 0.41 g (75.9%) of crystals of melting point 60°-62° C.

Workup

  1. customThe resulting reaction mixture
  2. customis chromatographed over a column of 30 g of silica gel 60 (mobile phase 99:1 CH2Cl2 /acetone, 0.3 bar excess pressure)

Sources & evidence

ORD record
ord-cadbda9725de44d7b7fdc329c488acb1
Source dataset
uspto-grants-1991_04
Patent number
US05011944

Reaction notes

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