Hydrochloric Acid → 2-(3-Methoxy-2-methylbenzyl)cyclohexanone

HRID 1067113Notes

Reaction equation

HRID 1067113 reaction equation
O[CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:11]=1[CH3:18])[CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9].Cl>C1COCC1.CCOC(C)=O>[CH3:17][O:16][C:12]1[C:11]([CH3:18])=[C:10]([CH:15]=[CH:14][CH:13]=1)[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=[O:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21196457HCID 21196457, compound

Product 1

HCID 183674192-(3-Methoxy-2-methylbenzyl)cyclohexanoneYield 56.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[hydroxy-(3-methoxy-2-methylphenyl)-methyl]cyclohexanone (1.85 g) in THF (20 ml) was added conc. HCl (0.5 ml) at 5° C. and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with EtOAc, washed with saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was dissolved in MeOH (30 ml) and 10% Pd/C (wet) (400 mg) was added. The mixture was stirred under hydrogen atmosphere at room temperature for 2 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was pufified by silica gel column chromatography (hexane-EtOAc 12:1 to 8:1) to give 2-(3-methoxy-2-methylbenzyl)cyclohexanone (980.6 mg) as an oil.

Workup

  1. washwashed with saturated sodium hydrogen carbonate, water, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in MeOH (30 ml)
  5. addition10% Pd/C (wet) (400 mg) was added
  6. stirringThe mixture was stirred under hydrogen atmosphere at room temperature for 2 hours
  7. customThe catalyst was removed by filtration
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-b03804560209470a91d2a6b85f3f9864
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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