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

HRID 968450Notes

Reaction equation

HRID 968450 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 and concentrated to give (R)-1-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. customThe combined organic extracts are dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f826766a437841db906d830abe64742a
Source dataset
uspto-grants-2007_12
Patent number
US07303739B2

Reaction notes

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