Methanol → 2-(4-Methoxy-3-methylphenyl)ethanol

HRID 1511890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511890
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][C:4]=1[CH3:13].CO.CCOC(C)=O.CCCCCCC>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][C:4]=1[CH3:13]

Komponenten

5

Edukt 3

HCID 887Methanol2×HCID 1382764-Methoxy-3-methylphenylacetic acidHCID 21899848Ethylacetate heptane

Produkt 1

HCID 534036562-(4-Methoxy-3-methylphenyl)ethanolAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(4-methoxy-3-methylphenyl)acetic acid (1 g, 5.55 mmol) was dissolved in Tetrahydrofuran (27.7 ml). A solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly under nitrogen. The reaction was stirred for about 18 h. Methanol was slowly added to quench the reaction The solution was rotovapped. More methanol was added. The solution was rotovapped. This was repeated twice. The solution was passed through a short pad of silica gel eluting with 1:1 EtOAc/heptane and then rotovapped to give 2-(4-methoxy-3-methylphenyl)ethanol (0.986 g, 5.93 mmol, 107% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.05 (m, 1H), 7.04 (m, 1H), 6.80 (m, 1H), 3.85 (s, 3H), 3.84 (t, 2H), 2.81 (t, 2H), 2.25 (s, 1H), 1.64 (s, 1H)

Aufarbeitung

  1. additionA solution of borane tetrahydrofuran complex (12.21 ml, 12.21 mmol) was added slowly under nitrogen
  2. customto quench
  3. customthe reaction The solution

Quellen und Nachweise

ORD-Eintrag
ord-770c1bfdc63047f78c54a56eb455096f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217027B2

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