Hydrochloric Acid → 4-(2-Methylphenyl)cyclohexanone

HRID 429717Notes

Reaction equation

HRID 429717 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])(O)[CH2:6][CH2:5]2)[O:3]C1.Cl.[H][H]>O1CCOCC1.[Pd]>[CH3:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 544507798-(o-Tolyl)-1,4-dioxaspiro[4.5]decan-8-olHCID 178418361HCID 178418361, compound

Product 1

HCID 183526694-(2-Methylphenyl)cyclohexanoneYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(2-methylphenyl)-4-hydroxycyclohexanone ethylene ketal from the preceding step in 800 mL dioxane was treated with 16 mL concentrated hydrochloric acid and 30 grams 10% palladium-on-carbon under 35 p.s.i. hydrogen for 24 hours, then filtered through Celite to remove the catalyst. The filtrate was treated with 230 mL water and stirred at room temperature for 48 hours. The solution was evaporated, the pH adjusted to 8 with saturated aqueous sodium bicarbonate solution, and extracted with methylene chloride. The organic layer was dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/hexanes as eluent to afford 33.3 grams (35%) of an oil.

Workup

  1. filtrationfiltered through Celite
  2. customto remove the catalyst
  3. additionThe filtrate was treated with 230 mL water
  4. customThe solution was evaporated
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-90f69e579b1f4065802ba9a229f178bf
Source dataset
uspto-grants-2001_11
Patent number
US06319915B1

Reaction notes

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