1-(2-Hydroxy-5-methoxyphenyl)ethan-1-one → 2-(2-Hydroxypropan-2-YL)-4-methoxyphenol

HRID 38362

Reaktionsgleichung

Reaktionsgleichung von HRID 38362
[CH3:1][Mg]Br.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[C:13](=[O:15])[CH3:14]>C1COCC1>[OH:15][C:13]([C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[OH:4])([CH3:1])[CH3:14]

Komponenten

4

Edukt 2

HCID 697141-(2-Hydroxy-5-methoxyphenyl)ethan-1-oneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 252417532-(2-Hydroxypropan-2-YL)-4-methoxyphenolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methylmagnesium bromide (221 ml, 665 mmol) in 800 ml THF at 0° C. was added 1-(2-hydroxy-5-methoxy-phenyl)-ethanone (20.21 g, 302 mmol) in portions over 30 min. The mixture was allowed to warm to room temperature. After 16 h the mixture was quenched by the slow addition of 10% NH4Cl, carefully acidified to pH=1 (slow addition) with concentrated HCl and extracted with Et2O. The combined organics were washed with H2O, washed with brine, died over MgSO4, filtered and concentrated in vacuo to give 2-(1-hydroxy-1-methyl-ethyl)-4-methoxy-phenol (50.57 g, 100%) as a tan solid.

Aufarbeitung

  1. customAfter 16 h the mixture was quenched by the slow addition of 10% NH4Cl
  2. additioncarefully acidified to pH=1 (slow addition) with concentrated HCl
  3. extractionextracted with Et2O
  4. washThe combined organics were washed with H2O
  5. washwashed with brine
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-78993c18a113412c8253f3f89bc0362a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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