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

HRID 21556

Reaktionsgleichung

Reaktionsgleichung von HRID 21556
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 5202412-Benzylpropane-1,3-diolAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5aa67c9da6f34c85ad1683c7ead164b5
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05424309

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