2,4-Dimethylphenol → Cyclohexyl 3,5-dimethyl-2-hydroxyphenyl ketone

HRID 2051404Notes

Reaction equation

HRID 2051404 reaction equation
[C:1]1([OH:9])[C:2]([CH3:8])=[CH:3][C:4]([CH3:7])=[CH:5][CH:6]=1.[CH:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:8][C:2]1[C:1]([OH:9])=[C:6]([C:16]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:17])[CH:5]=[C:4]([CH3:7])[CH:3]=1

Participants

4

Reactant 3

HCID 77712,4-DimethylphenolHCID 75938Cyclohexanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15094963Cyclohexyl 3,5-dimethyl-2-hydroxyphenyl ketoneYield 69.4%

Conditions

Temperature
110 °C

Procedure

A mixture of 194 g of 2,4-xylenol and 233 g of cyclohexylcarbonyl chloride was stirred at 110° C. for 1 hour and then thereto was gradually added 318 g of anhydrous aluminum chloride, followed by stirring for further 1 hour at 110° C. The reaction mixture was added to 2 liters of ice water and the organic layer was extracted with 2 liters of chloroform. The extract was washed successively with water and then with a saturated aqueous sodium chloride solution and thereafter dried with anhydrous magnesium sulfate. The chloroform was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: n-hexane) to obtain 256.2 g of cyclohexyl 3,5-dimethyl-2-hydroxyphenyl ketone. Brown oily substance.

Workup

  1. stirringby stirring for further 1 hour at 110° C
  2. extractionthe organic layer was extracted with 2 liters of chloroform
  3. washThe extract was washed successively with water
  4. dry with materialwith a saturated aqueous sodium chloride solution and thereafter dried with anhydrous magnesium sulfate
  5. distillationThe chloroform was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: n-hexane)

Sources & evidence

ORD record
ord-90057ae7abb345a4941e11891bdb887a
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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