Sulfuric Acid → Eucarvone

HRID 579727Notes

Reaction equation

HRID 579727 reaction equation
S(=O)(=O)(O)O.[CH3:6][C:7]1[C:12](=[O:13])[CH2:11][CH:10]([C:14]([CH3:16])=[CH2:15])[CH2:9][CH:8]=1.Br>C1(C)C=CC=CC=1>[CH3:6][C:7]1[C:12](=[O:13])[CH2:11][C:14]([CH3:15])([CH3:16])[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 20136300HCID 20136300, compound

Product 1

HCID 136330Eucarvone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 12 liter separatory funnel, 8 liters of ice/water and 122 ml sulfuric acid (concentrated) is placed. With stirring, the carvone hydrobromide reaction mixture is added to the reaction mass. 500 ml Toluene is then added to the reaction mass and the reaction mass is continued to be stirred. The reaction mass now exists in two phases; an aqueous phase and an organic phase. The aqueous phase is discarded and the organic phase is washed with 2 liters of water. The reaction mass is then added to a mixture of 200 ml saturated sodium bicarbonate and 1000 ml water. The resulting product has the structure: ##STR153## (crude reaction mass).

Workup

  1. additionis added to the reaction mass
  2. stirringto be stirred
  3. washthe organic phase is washed with 2 liters of water
  4. additionThe reaction mass is then added to a mixture of 200 ml saturated sodium bicarbonate and 1000 ml water
  5. custom##STR153## (crude reaction mass)

Sources & evidence

ORD record
ord-a1418f540de846248c93aa6e9bde4dd0
Source dataset
uspto-grants-1988_06
Patent number
US04749681

Reaction notes

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