Water → 1,2-Diphenylethanol

HRID 2293667Notes

Reaction equation

HRID 2293667 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C(OCC)C>[C:7]1([CH:13]([OH:14])[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 99482-PhenylacetophenoneHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride

Product 1

HCID 941781,2-Diphenylethanol

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 5.50 g of commercially available deoxybenzoin in 25.0 mL of diethyl ether. 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 0.5 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 5.50 g of the title product as off-white crystals. 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 0.5 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-9331531b4d02466da35f5ff1628c0e87
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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