Hydrochloric Acid → 1-(4-Cyclohexylphenyl)ethan-1-one

HRID 1777328Notes

Reaction equation

HRID 1777328 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:17](Cl)(=[O:19])[CH3:18].Cl>ClC(Cl)C>[CH:11]1([C:5]2[CH:6]=[CH:7][C:8]([C:17](=[O:19])[CH3:18])=[CH:9][CH:10]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 13229CyclohexylbenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 877151-(4-Cyclohexylphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Anhydrous aluminium chloride (1.65 g, 0.012 mol) is added to a solution of cyclohexyl benzene (1 g, 0.006 mol) and acetyl chloride (0.7 mL, 0.009 mol) in dichloroethane (10 mL) at −5° C. to 0° C. temperature. The reaction mixture is stirred at this temperature for 30 minutes and then treated with 2N hydrochloric acid (7 mL). It is extracted with dichloromethane (2×20 mL) and the combined extract is dried over sodium sulfate. After removing the solvent under reduced pressure the residue is purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 7:93) to get 1-(4-cyclohexylphenyl)ethanone.

Workup

  1. extractionIt is extracted with dichloromethane (2×20 mL)
  2. extractionthe combined extract
  3. dry with materialis dried over sodium sulfate
  4. customAfter removing the solvent under reduced pressure the residue
  5. customis purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 7:93)

Sources & evidence

ORD record
ord-2d8edd0f6c2b4e1293026bae2ae1abeb
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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