Benzeneacetic acid, alpha,alpha-dimethyl-, ethyl ester → beta,beta-Dimethylbenzeneethanol

HRID 1417794Notes

Reaction equation

HRID 1417794 reaction equation
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:3](OCC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH3:8][C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:1])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 232036Benzeneacetic acid, alpha,alpha-dimethyl-, ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 219535beta,beta-Dimethylbenzeneethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 2-methyl-2-phenylpropionate LIII, 4.50 g, 23.5 mmol) is added to lithium aluminum hydride (0.908 g, 23.5 mmol) in dry ether (100 ml) cooled at 0°. After stirring for 2.5 hr, the mixture is quenched by adding, successively, water (1 ml), aqueous sodium hydroxide (15%, 1 ml) and water (3 ml). After stirring for several minutes, the solids are filtered off and washed well with ether. The filtrate is washed twice with saline and the organic phase is separated, dried over magnesium sulfate and concentrated to give 2-methyl-2-phenylpropanol (XLV), NMR (CDCl3) 1.34, 3.62, 3.71, 7.22 and 7.31-7.41 6 δ.

Workup

  1. temperaturecooled at 0°
  2. customthe mixture is quenched
  3. additionby adding
  4. stirringAfter stirring for several minutes
  5. filtrationthe solids are filtered off
  6. washwashed well with ether
  7. washThe filtrate is washed twice with saline
  8. customthe organic phase is separated
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3a916157ebcd40569e1804f431cbdd04
Source dataset
uspto-grants-1999_03
Patent number
US05877317

Reaction notes

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