Water → 2-(3,4-Dimethylphenyl)ethanol

HRID 1742710Notes

Reaction equation

HRID 1742710 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:9]=[C:10]([CH2:15][C:16](OC)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14].O.[OH-].[Na+]>C(OCC)C>[CH3:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[CH3:14])[CH2:15][CH2:16][OH:17]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 17607842Methyl 2-(3,4-dimethylphenyl)acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 339432-(3,4-Dimethylphenyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminium hydride (0.4 g) was added in portions to a solution of methyl 3,4-dimethylphenylacetate (3.0 g--see Preparation 16) in anhydrous diethyl ether (50 ml). When the addition was complete, the mixture was heated under reflux for 1 hour then allowed to stand at room temperature for 16 hours. Water (0.5 ml) was carefully added dropwise followed by 15% aqueous sodium hydroxide (0.5 ml) and finally more water (2 ml). The resulting solid precipitate was filtered off and washed with diethyl ether (3×20 ml). The filtrate and washings were combined, dried (MgSO4) and concentrated in vacuo to give the title compound as a colourless oil which was used directly--see Preparation 18).

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. filtrationThe resulting solid precipitate was filtered off
  5. washwashed with diethyl ether (3×20 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b6a42ff8c3e4e4080ec9b74ca1cb90a
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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