Potassium Hydroxide → 2-Hydroxy-4,4,6,6-tetramethylcyclohex-2-en-1-one

HRID 1758013Notes

Reaction equation

HRID 1758013 reaction equation
[OH-:1].[K+].Br[CH:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][C:7]([CH3:13])([CH3:12])[CH:6](Br)[C:5]1=[O:15]>O>[OH:15][C:5]1[C:6](=[O:1])[C:7]([CH3:13])([CH3:12])[CH2:8][C:9]([CH3:11])([CH3:10])[CH:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 1027432,6-Dibromo-3,3,5,5-tetramethylcyclohexan-1-one

Product 1

HCID 5741832-Hydroxy-4,4,6,6-tetramethylcyclohex-2-en-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of potassium hydroxide (50 g) in 1500 ml of distilled water was added the brominated compound of step 1 (50 g). Stirring was continued for 24 hours. The solution was filtered to remove brominated compound which had not dissolved. The filtrate was cooled in an ice bath and concentrated sulphuric acid added dropwise until a white solid precipitated. The mixture was stirred for 30 minutes, after which the white solid was collected and recrystallized from a hot mixture of 200 ml of methanol and 100 ml of water, giving 2-hydroxy-4,4,6,6-tetramethylcyclohex-2-enone as white crystals, 13.5 g, melting range 85°-86° C.

Workup

  1. filtrationThe solution was filtered
  2. customto remove brominated compound which
  3. dissolutionhad not dissolved
  4. temperatureThe filtrate was cooled in an ice bath
  5. additionconcentrated sulphuric acid added dropwise until a white solid
  6. customprecipitated
  7. stirringThe mixture was stirred for 30 minutes
  8. customafter which the white solid was collected
  9. customrecrystallized from a hot mixture of 200 ml of methanol and 100 ml of water

Sources & evidence

ORD record
ord-174aa176362846b5a416204e57d67433
Source dataset
uspto-grants-1983_02
Patent number
US04371603

Reaction notes

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