Potassium Permanganate → 3-Chloro-4-cyclohexylbenzoic acid

HRID 1777332Notes

Reaction equation

HRID 1777332 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:20](=[O:22])C)[CH:11]=[CH:12][C:13]=1[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>O1CCOCC1>[Cl:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C:20]([OH:22])=[O:2]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 109006461-(3-Chloro-4-cyclohexylphenyl)ethanone

Product 1

HCID 203104163-Chloro-4-cyclohexylbenzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

An aqueous alkaline solution of potassium permanganate (2.94 g, 0.0186 mol; in 22 mL 12% aqueous sodium hydroxide) is added to solution of 1-(3-chloro-4-cyclohexylphenyl)ethanone (2.2 g, 0.0093 mol) in dioxane (11 mL). The reaction mixture is stirred at 80° C. temperature for 2 hrs. It is then filtered and the filtrate is washed with diethyl ether (2×10 mL). The pH of the aqueous layer is adjusted to 1-2 by using 6N hydrochloric acid. It is extracted in ethyl acetate (3×15 mL). Combined organic layer is dried over sodium sulfate and concentrated to get the crude, which is purified using column chromatography (230-400 mesh; ethyl acetate:n-hexane, 1:3) to yield 3-chloro-4-cyclohexyl benzoic acid.

Workup

  1. filtrationIt is then filtered
  2. washthe filtrate is washed with diethyl ether (2×10 mL)
  3. extractionIt is extracted in ethyl acetate (3×15 mL)
  4. dry with materialCombined organic layer is dried over sodium sulfate
  5. concentrationconcentrated
  6. customto get the crude, which
  7. customis purified

Sources & evidence

ORD record
ord-b661e3883d424e9fa748ca86e317c077
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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