Diethyl Ether → 1-(2-Methylphenyl)ethanol

HRID 1460377Notes

Reaction equation

HRID 1460377 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7](OCC)C.C[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].[H-]>C(OCC)(=O)C>[CH3:13][CH:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=1[CH3:7])[OH:15]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 71481-Phenyl-1-propanoneHCID 166653HydrideHCID 21226445Aluminium lithium hydride

Product 1

HCID 1109531-(2-Methylphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In a dry flask under nitrogen atomosphere was suspended 3.25 g (0.086 mol) lithium aluminum hydride and 250 ml of dry diethyl ether. The suspension was cooled in an ice/water bath, then 24.5 g (0.184 mol) of 2-methylacetophenone was added dropwise. After 12 hours the excess hydride was decomposed with 100 ml of ethyl acetate. The reaction mixture was washed with ammonium chloride solution and water. The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 25.0 g of a clear oil.

Workup

  1. customIn a dry flask under nitrogen atomosphere was suspended
  2. temperatureThe suspension was cooled in an ice/water bath
  3. washThe reaction mixture was washed with ammonium chloride solution and water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ae5d46eff4aa4ab7bc9650fb146d4c7d
Source dataset
uspto-grants-1991_12
Patent number
US05071469

Reaction notes

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