Diethyl phenylmalonate → 2-Phenyl-1,3-propanediol

HRID 589538

Reaktionsgleichung

Reaktionsgleichung von HRID 589538
[C:1]1([CH:7]([C:13](OCC)=[O:14])[C:8](OCC)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.P([O-])(O)(O)=O.[Na+].[BH4-].[Na+]>C(O)C>[C:1]1([CH:7]([CH2:8][OH:9])[CH2:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 66514Diethyl phenylmalonateHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 4311764Sodium borohydride

Produkt 1

HCID 2541782-Phenyl-1,3-propanediolAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 20 g of diethyl phenylmalonate, 6.6 g of sodium dihydrogen phosphate monohydrate and 140 ml of absolute ethanol was cooled to 15° C. after which 7.1 g of solid sodium borohydride was added. The reaction was completed by quenching the excess of sodium borohydride with 10% HCl solution and distilling the residual ethanol. 8 ml of NaOH 50% were added in order to obtain a pH of between about 8.0 to about 9.0. The obtained 2-phenyl-1,3-propanediol was then extracted into 400 ml of ethyl acetate. The organic layer was washed with 40 ml of water and filtered through alumina. The precipitate was crystallized from toluene following solvent removal, to obtain 8.9 g of 2-phenyl-1,3-propanediol with a yield of 69%.

Aufarbeitung

  1. additionwas added
  2. customby quenching the excess of sodium borohydride with 10% HCl solution
  3. distillationdistilling the residual ethanol
  4. addition8 ml of NaOH 50% were added in order
  5. customto obtain a pH of between about 8.0 to about 9.0
  6. extractionThe obtained 2-phenyl-1,3-propanediol was then extracted into 400 ml of ethyl acetate
  7. washThe organic layer was washed with 40 ml of water
  8. filtrationfiltered through alumina
  9. customThe precipitate was crystallized from toluene following solvent removal

Quellen und Nachweise

ORD-Eintrag
ord-1aa7a703d37545faafc82bfcca1a0a37
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233898B2

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