Acetic Acid → 2-Benzylpropane-1,3-diol

HRID 21556

Reaction equation

HRID 21556 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.[BH4-].[Na+].[Cl-].[Li+].C(O)(=O)C>C(O)C.C1COCC1>[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

7

Reactant 4

HCID 176Acetic AcidHCID 69090Diethyl 2-benzylpropanedioateHCID 433294Lithium ChlorideHCID 4311764Sodium borohydride

Product 1

HCID 5202412-Benzylpropane-1,3-diolYield 105.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5 g of diethyl benzylmalonate was dissolved in a mixture of 120 ml of ethanol and 80 ml of THF, and 3.8 g of sodium borohydride and 4.3 g of lithium chloride were added thereto under cooling with ice. The mixture was stirred at room temperature for 2 hours. Then, 5.8 ml of acetic acid was added thereto, and the solvent was distilled off under reduced pressure. Water and ethyl acetate were added to the residue. The ethyl acetate layer was separated, washed with water and with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3.5 g of 2-benzyl-1,3-propanediol as colorless solid.

Workup

  1. additionwere added
  2. temperatureunder cooling with ice
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater and ethyl acetate were added to the residue
  5. customThe ethyl acetate layer was separated
  6. washwashed with water and with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5aa67c9da6f34c85ad1683c7ead164b5
Source dataset
uspto-grants-1995_06
Patent number
US05424309

Linked notes

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