Methanol → HCID 9879261, compound

HRID 1797400Notes

Reaction equation

HRID 1797400 reaction equation
Br[C:2]([CH3:13])([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4].[CH3:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].CO>CS(C)=O.O>[CH3:12][C:2]([O:23][C:16]1[CH:17]=[C:18]([CH3:22])[CH:19]=[C:20]([CH3:21])[C:15]=1[CH3:14])([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 127692,3,5-TrimethylphenolHCID 113224292-bromo-2-methyl-1-(4-methylphenyl)-1-propanone

Product 1

HCID 9879261HCID 9879261, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

2-bromo-2-methyl-1-(4-methylphenyl)-1-propanone (422 g) in dimethyl sulfoxide (DMSO, 681 mL) was added dropwise to a solution of 2,3,5-trimethylphenol (136.19 g) and potassium carbonate (276.4 g) in DMSO (681 mL), followed by stirring at 35° C. for 24 hours. To the mixture were added dropwise methanol (953 mL) warmed to 55° C. and then water (953 mL). The mixture was stirred at 55° C. for 30 minutes and then at 40° C. for 1 hour. Precipitated crystals were filtered and suspended in methanol (2043 mL). Water (681 mL) was added to the suspension and the mixture was stirred at 40° C. for 1 hour. Precipitated crystals were filtered to obtain the title compound (257.98 g, 87%).

Workup

  1. temperaturewarmed to 55° C.
  2. stirringThe mixture was stirred at 55° C. for 30 minutes
  3. waitat 40° C. for 1 hour
  4. customPrecipitated crystals
  5. filtrationwere filtered
  6. additionWater (681 mL) was added to the suspension
  7. stirringthe mixture was stirred at 40° C. for 1 hour
  8. customPrecipitated crystals
  9. filtrationwere filtered

Sources & evidence

ORD record
ord-a21c32e589b7403eb94f4a7145d74c50
Source dataset
uspto-grants-2006_04
Patent number
US07034166B2

Reaction notes

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