Acetone → p-Cymen-8-ol

HRID 591119Notes

Reaction equation

HRID 591119 reaction equation
BrC1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][C:10]([CH3:12])=[O:11].[CH2:13]1COCC1>>[CH3:8][C:5]1[CH:6]=[CH:7][C:9]([C:10]([OH:11])([CH3:13])[CH3:12])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 78054-BromotolueneHCID 8028Tetrahydrofuran

Product 1

HCID 14529p-Cymen-8-ol

Procedure

In a clean RB flask, fitted with reflux condenser Mg (3.5 g, 0.1462 mol) was taken and added THF (125 ml) followed by slow addition of 4-bromo toluene (25 g, 0.1462 mol) for about 1 hr. The reaction mixture was then stirred at room temperature for about 3 h. Then into this slowly added acetone (10.7 mL, 0.1462 mol) and stirred at room temperature for about 2 hrs. After completion of the reaction as indicated by TLC, reaction mixture was then cooled to 0° C. and quenched with Sat ammonium chloride solution (30 ml) and extracted with ethyl acetate. Combined organic layer was dried over Na2SO4 and conc. Under reduced pressure to get the crude product (8-hydroxy p-cymene, 18.2 g).

Workup

  1. customIn a clean RB flask, fitted
  2. customAfter completion of the reaction
  3. customas indicated by TLC, reaction mixture
  4. temperaturewas then cooled to 0° C.
  5. customquenched with Sat ammonium chloride solution (30 ml)
  6. extractionextracted with ethyl acetate
  7. dry with materialCombined organic layer was dried over Na2SO4 and conc. Under reduced pressure

Sources & evidence

ORD record
ord-01c21b0b0c6342a8b37dd5dfab1156f6
Source dataset
uspto-grants-2016_01
Patent number
US09238609B2

Reaction notes

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