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

HRID 353409Notes

Reaction equation

HRID 353409 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-A1) 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-496cb09ef102473ba583754da63af460
Source dataset
uspto-grants-2004_06
Patent number
US06752981B1

Reaction notes

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