HCID 642459, compound → HCID 86745602, compound

HRID 2372915Notes

Reaction equation

HRID 2372915 reaction equation
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[C:6]([CH3:9])=[CH:5][C:4](=[O:10])[C:3]1=[O:11]>Cl>[OH:10][C:4]1[C:3](=[O:11])[C:2]([CH3:12])([CH3:1])[C:7](=[O:8])[C:6](=[CH:9][CH:9]=[C:6]2[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[C:3](=[O:11])[C:4]([OH:10])=[CH:5]2)[CH:5]=1

Participants

3

Reactant 1

HCID 642459HCID 642459, compound

Product 1

HCID 86745602HCID 86745602, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

In a 2-1 three-neck flask equipped with an intensive condenser and a stirrer, 50 g of 3,3,5-trimethylcyclohex-5-ene-1,2,4-trione (from Example 2) were dissolved in 300 ml of concentrated hydrochloric acid at room temperature. The flask was then dipped into a hot oil bath at 100° C. for 15 minutes, in the course of which the reaction mixture turned dark and an orange precipitate formed. This solid precipitate was filtered off with suction while hot and washed with water, ethanol, acetone, ethyl acetate and ether. The resulting product was freed of adhering solvent residues in a desiccator. (It is pure enough in this state for further reactions. If desired, it can be recrystallized from dioxane.)

Workup

  1. customIn a 2-1 three-neck flask equipped with an intensive condenser and a stirrer
  2. customan orange precipitate formed
  3. filtrationThis solid precipitate was filtered off with suction while hot and
  4. washwashed with water, ethanol, acetone, ethyl acetate and ether
  5. customThe resulting product was freed of adhering solvent residues in a desiccator
  6. customit can be recrystallized from dioxane

Sources & evidence

ORD record
ord-df1d90ecb3724b6dab3d91eace18b158
Source dataset
uspto-grants-1992_03
Patent number
US05101032

Reaction notes

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