2-Phenylisobutyric acid → beta,beta-Dimethylbenzeneethanol

HRID 1810052Notes

Reaction equation

HRID 1810052 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:12])[C:9](O)=[O:10]>C1COCC1>[CH3:12][C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:7])[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 132222-Phenylisobutyric acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 219535beta,beta-DimethylbenzeneethanolYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (4.64 g, 123.0 mmol) in dry THF (500 mL) was added 2-methyl-2-phenyl-propionic acid (20.0 g, 123.0 mmol) in dry THF (250 mL) dropwise at 55° C. over 10 min. The mixture was quenched with sodium hydroxide aqueous solution (60 mL, 15%). The mixture was filtered and the filtrate was dried over anhydrous sodium sulfate, filtered and evaporated to yield 2-methyl-2-phenyl-propan-1-ol (13.3 g, 72.7%), which was used to the next step without further purification.

Workup

  1. customThe mixture was quenched with sodium hydroxide aqueous solution (60 mL, 15%)
  2. filtrationThe mixture was filtered
  3. dry with materialthe filtrate was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-70a15294d0e24e53b9142ebb3fd6eb18
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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