Diphenylacetic Acid → beta-Phenylphenethyl alcohol

HRID 981456

Reaction equation

HRID 981456 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8](O)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][OH:9])[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 8333Diphenylacetic AcidHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 74662beta-Phenylphenethyl alcoholYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a rapidly stirring solution of 8.5 g (40 mmol) diphenyl acetic acid in 100 mL dry THF, at room temperature, was added 3.04 g (80 mmol) of LAH. The suspension was stirred at room temperature for 1 hour and then cooled to 0 degrees C. The excess LAH was decomposed by slow addition of 10% NaOH (200 mL aqueous solution). The product was extracted with AcOEt, dried over MgSO4 and concentrated under vacuum to yield 7.1 g (90%) of 2,2-diphenyl ethanol (12).

Workup

  1. temperaturecooled to 0 degrees C
  2. extractionThe product was extracted with AcOEt
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-07b91252976543058352788b7cc48a8c
Source dataset
uspto-grants-1991_02
Patent number
US04992421

Linked notes

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