Water → 2-[2-(Hydroxymethyl)phenyl]ethanol

HRID 1264538

Reaktionsgleichung

Reaktionsgleichung von HRID 1264538
[C:1](O)(=[O:12])[CH2:2][C:3]1[C:4](=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:5](O)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:6][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[CH2:2][CH2:1][OH:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 66643Homophthalic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 2390242-[2-(Hydroxymethyl)phenyl]ethanolAusbeute 98.293,703 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Dissolve homophthalic acid (22.2 g, 0.123 mmol) in tetrahydrofuran (250 mL) and add dropwise at room temperature to a slurry of lithium aluminum hydride (15.5 g, 0.407 mol) in tetrahydrofuran (500 mL). Heat at reflux for 18 hours, cool in an ice bath and carefully add, by dropwise addition, water (16 mL), followed by 50% sodium hydroxide (16 mL). Remove the ice bath, add water slowly with stirring and stir until the gray precipitate turns white and evolution of gas ceases. Filter, wash solids with methylene chloride, dry (MgSO4) and evaporate the solvent in vacuo to give 2-(2-hydroxymethyl-phenyl)-ethanol as a viscous oil (18.4 g, 98%).

Aufarbeitung

  1. temperatureHeat
  2. temperatureat reflux for 18 hours
  3. temperaturecool in an ice bath
  4. customRemove the ice bath
  5. additionadd water slowly
  6. stirringstir until the gray precipitate
  7. filtrationFilter
  8. washwash solids with methylene chloride
  9. dry with materialdry (MgSO4)
  10. customevaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e52eb7fbee254d6497bd77c6e8f39366
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06544980B2

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