Acetone → (2-(Benzyloxy)-3-methoxyphenyl)methanol

HRID 260081

Reaktionsgleichung

Reaktionsgleichung von HRID 260081
[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O>C(O)C>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 12680872-(Benzyloxy)-3-methoxybenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 927250(2-(Benzyloxy)-3-methoxyphenyl)methanolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 43.00 g (0.18 mole) of 2-benzyloxy-3-methoxy-benzaldehyde of Example 1 in 300 mL of absolute ethanol is treated, with stirring, with 7.56 g (0.20 mole) of sodium borohydride. The temperature rises to 50° C. After one-half hour 10 mL of acetone is added, keeping the temperature at less than 60° C. with cooling. After 15 minutes the volatiles are stripped off at reduced pressure. Ice water (500 mL) is added and the product is extracted into 600 mL of ethyl acetate. The dried (NA2SO4) solution is concentrated. The remaining oil is dissolved in 100 mL of warm ether. Petroleum ether is added to turbidity to give 37.70 g (86% yield) of pure product; mp 58°-60° C.

Aufarbeitung

  1. customrises to 50° C
  2. customat less than 60° C.
  3. temperaturewith cooling
  4. extractionthe product is extracted into 600 mL of ethyl acetate
  5. customThe dried (NA2SO4) solution
  6. concentrationis concentrated
  7. dissolutionThe remaining oil is dissolved in 100 mL of warm ether
  8. additionPetroleum ether is added to turbidity

Quellen und Nachweise

ORD-Eintrag
ord-f760b7f1e7ff433698dbe74588dcb3ae
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05525614

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