Methanol → beta,beta-Dimethylbenzeneethanol

HRID 74012

Reaktionsgleichung

Reaktionsgleichung von HRID 74012
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3](O)=[O:4].CSC.B.CO.O>C1COCC1>[CH3:6][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:1])[CH2:3][OH:4]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 132222-Phenylisobutyric acidHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 219535beta,beta-DimethylbenzeneethanolAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-2-phenyl-propionic acid (82 g, 0.5 mol) in THF (200 mL) was added dropwise borane-dimethyl sulfide (2M, 100 mL) at 0-5° C. The mixture was stirred at this temperature for 30 min and then heated at reflux for 1 h. After cooling, methanol (150 mL) and water (50 mL) were added. The mixture was extracted with EtOAc (100 mL×3), and the combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated to give 2-methyl-2-phenyl-propan-1-ol as an oil (70 g, 77%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 h
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with EtOAc (100 mL×3)
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b19017f1db594f9c818466d35370075d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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