Water → 4,4-Diphenylbutan-1-ol

HRID 565650Notes

Reaction equation

HRID 565650 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:15][C:16](O)=[O:17])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C(OCC)C>[C:19]1([CH:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14][CH2:15][CH2:16][OH:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 2743834,4-Diphenylbutanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 925194,4-Diphenylbutan-1-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 70 mL of ice-cooled diethyl ether was suspended 1.9 g of lithium aluminum hydride, followed by dropwise addition of a solution of 4,4-diphenylbutyric acid (6.0 g) in diethyl ether (50 mL). After completion of dropwise addition, the mixture was refluxed for 2 hours and, then, allowed to cool. To this reaction mixture, 1.9 mL of water, 1.9 mL of 15% aqueous sodium hydroxide, and 5.7 mL of water were added in the order mentioned and the mixture was stirred at room temperature for 30 minutes. The precipitate was filtered off and the filtrate was concentrated to provide 5.6 g of the title compound. Yield 99%.

Workup

  1. additionAfter completion of dropwise addition
  2. temperaturethe mixture was refluxed for 2 hours
  3. temperatureto cool
  4. filtrationThe precipitate was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-70974a9ac1214b46ae7221f29d3a0010
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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