Toluene → (R)-(+)-1-Phenyl-1,3-propanediol

HRID 1182781Notes

Reaction equation

HRID 1182781 reaction equation
[H-].COCCO[Al+]O[CH2:9][CH2:10][O:11]C.[Na+].[H-].[C:15]1([CH3:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(COC)[O:23]C>CCOCC>[C:15]1([C@H:21]([OH:23])[CH2:9][CH2:10][OH:11])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 80711,2-DimethoxyethaneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 2735120(R)-(+)-1-Phenyl-1,3-propanediol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of commercial (−)-(2S,3S)-2,3-epoxycinnamyl alcohol (10.0 mmol) in dimethoxyethane (50 mL) is added a 3.4 M solution of sodium bis(2-methoxyethoxy)aluminum hydride (Red-Al) in toluene (10.5 mmol) dropwise under nitrogen at 0° C. After stirring at room temperature for 3 h, the solution is diluted with ether and quenched with 5% HCl solution. After further stirring at room temperature for 30 min, the white precipitate formed is removed by filtration and boiled with ethyl acetate and filtered again. The combined organic extracts are dried with magnesium sulfate and concentrated to give (R)-3-phenyl-1,3-dihydroxypropane.

Workup

  1. customquenched with 5% HCl solution
  2. stirringAfter further stirring at room temperature for 30 min
  3. customthe white precipitate formed
  4. customis removed by filtration
  5. filtrationfiltered again
  6. dry with materialThe combined organic extracts are dried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0fbfb94bcc4941739007fa1d7d904dd6
Source dataset
uspto-grants-2014_03
Patent number
US08664195B2

Reaction notes

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