Cyclohexanol → HCID 19102191, compound

HRID 1974677Notes

Reaction equation

HRID 1974677 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+].[CH:18]1([OH:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(C(C)=O)C>[Cl:9][C:6]1[C:7](=[O:8])[C:1]([O:24][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[C:2]([Cl:11])[C:3](=[O:4])[C:5]=1[Cl:10]

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 8371ChloranilHCID 516892Sodium Bicarbonate

Product 1

HCID 19102191HCID 19102191, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Conditions

Temperature
55 °C

Procedure

Chloranil (0.06 mole) and sodium hydrogen carbonate (0.075 mole) were added to 300 ml of methyl ethyl ketone (MEK). The mixture was heated to 55° C. before adding cyclohexanol (0.5 mole) dropwise with stirring. When the reaction was complete (as judged by HPLC) the MEK solvent was removed from the product mixture under vacuum. The resultant orange gum was recrystallised from petroleum ether to provide the bright orange crystalline title product (0.04 moles).

Workup

  1. customwas removed from the product mixture under vacuum
  2. customThe resultant orange gum was recrystallised from petroleum ether

Sources & evidence

ORD record
ord-2c905be5e389414995c8fb7abd94e4d6
Source dataset
uspto-grants-1994_02
Patent number
US05283355

Reaction notes

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