1,3-Diphenyl-2-propanone → 1,3-Diphenyl-2-propanol

HRID 2293671

Reaction equation

HRID 2293671 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][C:14]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(OCC)C>[C:17]1([CH2:16][CH:14]([OH:15])[CH2:13][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 75931,3-Diphenyl-2-propanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1384781,3-Diphenyl-2-propanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirring suspension of 1.10 g of lithium aluminum hydride in 50 mL of diethyl ether under an argon atmosphere at 0° C. is slowly added a solution of 5.30 g of commercially available 1,3-diphenylacetone in 10.0 mL of diethyl ether with a 10 mL rinse. After 0.25 hours the grey suspension is warmed to room temperature. After 1.5 hours the reaction mixture is re-cooled to 0° C. and slowly treated with 1.2 mL of water followed by 5.0 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 5.2 g, of the title product as a viscous, clear, colorless oil. This product may be used directly in the next reaction without further purification. Physical characteristics are as follows:

Workup

  1. washrinse
  2. temperatureAfter 1.5 hours the reaction mixture is re-cooled to 0° C.
  3. additionslowly treated with 1.2 mL of water
  4. filtrationAfter 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customto afford 5.2 g

Sources & evidence

ORD record
ord-83daefa5813c43aeb366407e5f4eed69
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Linked notes

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