Water → Benzeneethanol,.alpha.,.be

HRID 2169193Notes

Reaction equation

HRID 2169193 reaction equation
C[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:7])[C:3]([O:5]C)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].O1CCC[CH2:24]1>>[CH3:24][CH:3]([OH:5])[CH:2]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7]

Participants

6

Reactant 5

HCID 962Water2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 143498Methyl 2-methyl-2-phenylpropanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 562145Benzeneethanol,.alpha.,.beYield 99%

Conditions

Temperature
0 °C

Procedure

Methyl 2-methyl-2-phenylpropanoate (10.8 g, 60.6 mmol, Eq: 1.00) in tetrahydrofuran (193 ml) was cooled to 0° C., lithium aluminium hydride was added (30.3 ml, 60.6 mmol, Eq: 1.00) via a syringe over 5 minutes. The mixture was stirred at 0° C. for 3 hours, and 2.3 ml water was added over 2 minutes. The mixture was stirred for 10 minutes, 2.3 ml 1N NaOH was added, the mixture was stirred for 5 minutes (a gel forms), 7 ml water was added, the mixture was stirred for 15 minutes, filtered through a pad of celite. The celite was washed with ether and the solvent was removed under vacuum to give methyl-2-phenyl-propan-1-ol (51) (9.0 g, 99%) as a clear oil.

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. additionwas added
  3. stirringthe mixture was stirred for 15 minutes
  4. filtrationfiltered through a pad of celite
  5. washThe celite was washed with ether
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-225f4b00809443c4844ec1b85330daad
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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