2,2-Diphenylpropionic acid → Benzeneethanol, β-methyl-β-phenyl-

HRID 1779914Notes

Reaction equation

HRID 1779914 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([CH3:17])[C:14](O)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O1CCCC1.O.[OH-].[Na+].C(OCC)C>[C:18]1([C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)([CH3:17])[CH2:14][OH:15])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 2

HCID 796762,2-Diphenylpropionic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 602279Benzeneethanol, β-methyl-β-phenyl-Yield 94%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a cold (0° C.) mixture of 4.3 g (114 mmol) of lithium aluminum hydride in 100 ml of tetrahydrofuran, was added 10.74 g (47 mmol) of 2,2-diphenylpropanoic acid in portions. The resulting reaction mixture was allowed to warm to room temperature. When the reaction was substantially complete, as indicated by thin layer chromatography (TLC), the reaction mixture was diluted with approximately 10 ml of water, 8 ml of 1N sodium hydroxide and diethyl ether and stirred for ninety minutes at 0° C. The reaction mixture was then poured over celite, and washed sequentially with diethyl ether and eluted using a gradient eluent of 5-20% ethyl acetate in hexane. The fractions containing the desired compound were combined and concentrated in vacuo to provide 9.38 g of material.

Workup

  1. customThe resulting reaction mixture
  2. additionThe reaction mixture was then poured over celite
  3. washwashed sequentially with diethyl ether
  4. washeluted
  5. additionThe fractions containing the desired compound
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b09f130b58a74881a82d8db85de1cbab
Source dataset
uspto-grants-1997_05
Patent number
US05629290

Reaction notes

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