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

HRID 368813

Reaction equation

HRID 368813 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 (XXXVIII, 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 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-e25ed6d082fa4a168dbeaf94ace4da92
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Linked notes

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