Sulfuric Acid → Cyclohexyl methyl ketone

HRID 848672Notes

Reaction equation

HRID 848672 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O.[OH:17][CH:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH3:19]>O>[CH3:19][C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:17]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 25408Sodium DichromateHCID 1378291-Cyclohexylethanol

Product 1

HCID 13207Cyclohexyl methyl ketoneYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Into a two-liter, round bottom, three-necked flask equipped with a condenser, a mechanical stirrer, thermometer and a liquid addition funnel were placed 900 ml. of water, 200 g. (0.67 mole) of technical grade sodium dichromate followed by 176 g. (1.8 mole) of concentrated sulfuric acid. The contents were cooled to 55°-60° C. and 120 g. (0.94 mole) of 1-hydroxyethylcyclohexane was added over a period of 1 hour, holding the temperature between 55°-50° C. by means of external cooling. After the alcohol had been added, the reaction mixture was allowed to stir for an additional 30 minutes and then 600 ml. of water was added and the contents heated to remove the ketone by steam distillation. When no more ketone was being steam distilled, the heat was removed, the distillate of water and ketone separated and the upper organic layer was distilled under vacuum collecting the fraction boiling at 115°-116° C. There was obtained 76 g. of ketone representing a 64% yield.

Workup

  1. customInto a two-liter, round bottom, three-necked flask equipped with a condenser, a mechanical stirrer
  2. additionthermometer and a liquid addition funnel
  3. temperatureThe contents were cooled to 55°-60° C.
  4. custombetween 55°-50° C.
  5. temperaturethe contents heated
  6. customto remove the ketone
  7. distillationby steam distillation
  8. distillationdistilled
  9. customthe heat was removed
  10. customthe distillate of water and ketone separated
  11. distillationthe upper organic layer was distilled under vacuum
  12. customcollecting the fraction boiling at 115°-116° C
  13. customThere was obtained 76 g

Sources & evidence

ORD record
ord-f39c2e22da714d2dacce336b7263fe85
Source dataset
uspto-grants-1981_10
Patent number
US04297269

Reaction notes

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