Diethyl Ether → 2-(2-Methylphenyl)cyclohexan-1-one

HRID 2218558Notes

Reaction equation

HRID 2218558 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[OH:13].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)C>ClCCl>[C:1]1([CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 159087TriacetoxyperiodinaneHCID 2513132-(o-Tolyl)cyclohexanol

Product 1

HCID 30480412-(2-Methylphenyl)cyclohexan-1-oneYield 54.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (cis/trans) 2-o-tolyl-cyclohexanol (1 g) in dichloromethane (30 ml) was added Dess-Martin periodinane (Aldrich 27,462-3) at room temperature. The reaction mixture was allowed to stir at room temperature for 16 hours before diethyl ether was added. The volume of solvent was reduced in vacuo to about one quarter of the initial amount. More diethylether (87 ml) was added and the solution was washed with a 10% solution of sodium thiosulfate (87 ml), a solution of saturated sodium bicarbonate (87 ml), brine (100 mL) and water (100 ml). The organic phase was then dried over sodium sulfate and concentrated in vacuo. The residue was then purified by column chromatography to give 0.54 g of 2-o-tolyl-cyclohexanone MS (EI) 188.2 (M+).

Workup

  1. additionwas added
  2. washthe solution was washed with a 10% solution of sodium thiosulfate (87 ml)
  3. dry with materialThe organic phase was then dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was then purified by column chromatography

Sources & evidence

ORD record
ord-647fccf5f7c94a3897c582ba380fba0b
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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