Water → Fenipentol

HRID 2293663Notes

Reaction equation

HRID 2293663 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])[CH2:8][CH2:9][CH2:10][CH3:11].O.[OH-].[Na+]>C(OCC)C>[C:13]1([CH:7]([OH:12])[CH2:8][CH2:9][CH2:10][CH3:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 66093ValerophenoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 3338Fenipentol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring suspension of 1.20 g of lithium aluminum hydride in 100 mL of diethyl ether under an argon atmosphere at 0° C. is slowly added a solution of 4.40 mL of commercially available valerophenone in 5.0 mL of diethyl ether over 10 minutes. After 0.5 hours the grey suspension is warmed to room temperature. After 1 hour the reaction mixture is re-cooled to 0° C. and slowly treated with 1.25 mL of water followed by 5.50 mL of 1N sodium hydroxide. After 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings. The filtrate is concentrated under reduced pressure to afford 4.5 g of 1-phenyl-1-pentanol as a clear, colorless oil. This product may be used directly in the next reaction without further purification.

Workup

  1. temperatureAfter 1 hour the reaction mixture is re-cooled to 0° C.
  2. filtrationAfter 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings
  3. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-7d4ef4362f764e5688a9d1aa18444ac3
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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