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

HRID 1047195Notes

Reaction equation

HRID 1047195 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]Br.[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 178418573HCID 178418573, compound

Product 1

HCID 2440052-(2-Methylphenyl)propan-2-olYield 88%

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 2 M methylmagnesium bromide in tetrahydrofuran (550 ml) is slowly added dropwise at below 0° C. After the addition, the reactant solution is stirred at room temperature for 3 hours under the detection of 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 resulted 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 out using rotary evaporator to obtain 132 g of 2-ortho-methylphenyl-2-propanol as a light yellow sticky liquid, with a yield of 88%.

Workup

  1. additionis slowly added dropwise at below 0° C
  2. additionAfter the addition
  3. stirringstirred until no bubbling from the solution
  4. extractionThe resulted 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 out
  9. customevaporator

Sources & evidence

ORD record
ord-db14f30b0fdd40579c84c3f9bbc33686
Source dataset
uspto-grants-2013_10
Patent number
US08569508B2

Reaction notes

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