Acetone → 2-(2,4,6-Trimethylphenyl)propan-2-ol

HRID 1261567Notes

Reaction equation

HRID 1261567 reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[Mg]Br.[CH3:12][C:13]([CH3:15])=[O:14].[NH4+].[Cl-]>O>[CH3:11][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[C:13]([OH:14])([CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 178425415HCID 178425415, compound

Product 1

HCID 2930032-(2,4,6-Trimethylphenyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

According to Example 3, mesitylmagnesium bromide (1.20 M in THF; 1.83 mL; 2.20 mmol; 1.10 equiv) was placed in a flame dried schlenk flask under an argon atmosphere and cooled to 0° C. At this temperature, LaCl3.2LiCl (0.33 M; 6.06 mL, 2.00 mmol, 1.00 equiv) was slowly added. The resulting mixture was allowed to warm up to room temperature and stirred for 4 h. Then, after cooling to 0° C., acetone (116 mg; 2.00 mmol) was added and the reaction was warmed up to room temperature and stirred for another hour at this temperature. When the end of the reaction was reached (GC-monitoring of aliquots), sat. aq. NH4Cl (2 mL) and water (2 mL) were added. The aqueous layer was extracted with ether (4×10 mL), the combined extracts were dried (Na2SO4) and evaporated in vacuo. Column chromatographical purification (silica; pentane:Et2O 9:1) afforded the desired product as colorless, crystalline solid, mp=106−107° C. (245 mg, 69%).

Workup

  1. customdried schlenk flask under an argon atmosphere
  2. addition2LiCl (0.33 M; 6.06 mL, 2.00 mmol, 1.00 equiv) was slowly added
  3. temperatureto warm up to room temperature
  4. temperatureThen, after cooling to 0° C.
  5. temperaturethe reaction was warmed up to room temperature
  6. stirringstirred for another hour at this temperature
  7. additionwere added
  8. extractionThe aqueous layer was extracted with ether (4×10 mL)
  9. dry with materialthe combined extracts were dried (Na2SO4)
  10. customevaporated in vacuo
  11. customColumn chromatographical purification (silica; pentane:Et2O 9:1)

Sources & evidence

ORD record
ord-9917a948ddf249b3811b9a7188cac0f0
Source dataset
uspto-grants-2013_06
Patent number
US08470982B2

Reaction notes

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