2-Methylacetophenone → 2-(2-Methylphenyl)propan-2-ol

HRID 1047196Notes

Reaction equation

HRID 1047196 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[CH3:11][Mg]Cl.[NH4+].[Cl-]>O1CCCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([OH:10])([CH3:11])[CH3:9]

Participants

5

Reactant 3

HCID 113402-MethylacetophenoneHCID 25517Ammonium ChlorideHCID 178418332HCID 178418332, compound

Product 1

HCID 2440052-(2-Methylphenyl)propan-2-olYield 82.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under the protection by nitrogen, ortho-methylphenylethanone (134 g, 1.0 mol) is dissolved in 1000 ml of tetrahydrofuran and then cooled to −5° C., into which 2M methylmagnesium chloride in tetrahydrofuran (550 ml) is slowly added dropwise at below 0° C. After the addition, the reactant solution is stirred at room temperature for 4 hours under the detection by TLC. When the reaction is complete, 200 ml of saturated NH4Cl solution is slowly added dropwise into the reactant solution and stirred until no bubbling from the solution. The reactant solution is then extracted by dichloromethane (500 ml×3), the extracts are combined, dried by anhydrous sodium sulfate, absorbed by activated carbon, filtered and then the solvent is distilled using rotary evaporator to obtain 124 g of 2-ortho-methylphenyl-2-propanol as a light yellow sticky liquid, with a yield of 82.6%.

Workup

  1. additionis slowly added dropwise at below 0° C
  2. additionAfter the addition
  3. stirringstirred until no bubbling from the solution
  4. extractionThe reactant solution is then extracted by dichloromethane (500 ml×3)
  5. dry with materialdried by anhydrous sodium sulfate
  6. customabsorbed by activated carbon
  7. filtrationfiltered
  8. distillationthe solvent is distilled
  9. customevaporator

Sources & evidence

ORD record
ord-50ff995a50e24d018fde618c13aadbf4
Source dataset
uspto-grants-2013_10
Patent number
US08569508B2

Reaction notes

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