Sodium Hydroxide → 2-Benzylpropane-1,3-diol

HRID 1939890Notes

Reaction equation

HRID 1939890 reaction equation
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>CCOCC>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 69090Diethyl 2-benzylpropanedioateHCID 21226445Aluminium lithium hydride

Product 1

HCID 5202412-Benzylpropane-1,3-diolYield 63.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Slowly add a solution of diethyl 2-benzylmalonate (20 g) in Et2O (300 mL) to a slurry of LiAlH4 (6 g) in Et2O (300 mL), then heat the reaction mixture at reflux for 14 h. Carefully add 4N NaOH to the reaction mixture until there is no precipitate, then extract with EtOAc. Concentrate the organic layer and purify the crude product on a silica gel column, eluting with EtOAc to obtain 2-benzyl-1,3-propanediol (8.45 g).

Workup

  1. temperatureheat the reaction mixture
  2. temperatureat reflux for 14 h
  3. extractionextract with EtOAc
  4. concentrationConcentrate the organic layer
  5. custompurify the crude product on a silica gel column
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-88bac1799d3a4ae4a0f6d84a9b4445e2
Source dataset
uspto-grants-1997_12
Patent number
US05698548

Reaction notes

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