Water → beta,beta-Dimethylbenzeneethanol

HRID 704418

Reaction equation

HRID 704418 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[C:9](OC)=[O:10].O>O1CCCC1>[CH3:13][C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:7])[CH2:9][OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 143498Methyl 2-methyl-2-phenylpropanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 219535beta,beta-Dimethylbenzeneethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (1.71 g) in tetrahydrofuran (50 ml) was dropwise added a solution of methyl 2-methyl-2-phenylpropionate (7.97 g) in tetrahydrofuran (20 ml) under ice cooling and the mixture was stirred at room temperature for 30 minutes. To the reaction solution was dropwise added water and then a saturated aqueous solution of sodium bicarbonate, and the solution was extracted with ether. The ehter layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel (100 g) column chromatography. Elution with a mixture solution of hexane-ethyl acetate (2:1) gave 6.32 9 of 2-methyl-2-phenylpropanol.

Workup

  1. extractiona saturated aqueous solution of sodium bicarbonate, and the solution was extracted with ether
  2. washThe ehter layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washElution with a mixture solution of hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-74fac3b8acdc4e79b0b153b118433d96
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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