(+-)-2-Butanol → 2-[(Butan-2-yl)oxy]-3,5,6-trichlorocyclohexa-2,5-diene-1,4-dione

HRID 1974678Notes

Reaction equation

HRID 1974678 reaction equation
[C:1]1(Cl)[C:7](=[O:8])[C:6]([Cl:9])=[C:5]([Cl:10])[C:3](=[O:4])[C:2]=1[Cl:11].C(=O)([O-])O.[Na+].[CH3:18][CH:19]([OH:22])[CH2:20][CH3:21]>CCC(C)=O>[Cl:9][C:6]1[C:7]([C:1]([O:22][CH:19]([CH2:20][CH3:21])[CH3:18])=[C:2]([Cl:11])[C:3](=[O:4])[C:5]=1[Cl:10])=[O:8]

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 8371ChloranilHCID 516892Sodium Bicarbonate

Product 1

HCID 191021892-[(Butan-2-yl)oxy]-3,5,6-trichlorocyclohexa-2,5-diene-1,4-dioneYield 86%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Chloranil (12.3 parts) was dissolved in MEK (300 parts) before adding sodium hydrogen carbonate (8 parts). Aqueous butan-2-ol (50 parts, 1:1) was then added and the mixture was stirred at room temperature until no starting material remained. At the end of the reaction the filtered solution was shown by HPLC to contain 86% title product. The product was used in subsequent reactions without isolation.

Workup

  1. customAt the end of the reaction the filtered solution

Sources & evidence

ORD record
ord-02602ba1a7394d668750437e19740dd2
Source dataset
uspto-grants-1994_02
Patent number
US05283355

Reaction notes

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