Hydrochloric Acid → 4-(2-Hydroxy-2-methylpropyl)phenol

HRID 19379

Reaktionsgleichung

Reaktionsgleichung von HRID 19379
C[Mg]Br.[OH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=[O:14])[CH3:13])=[CH:7][CH:6]=1.[C:15](OCC)(=O)C.Cl>O1CCCC1.O>[OH:14][C:12]([CH3:15])([CH3:13])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 70192744-HydroxyphenylacetoneHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 134818074-(2-Hydroxy-2-methylpropyl)phenolAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of methyl magnesium bromide (3 M, 14 mL, 39.94 mmol) cooled to 0° C. was added tetrahydrofuran (10 mL) and as solution of 1-(4-hydroxy-phenyl)-propan-2-one (1 g, 6.66 mmol) in tetrahydrofuran (30 mL). The resulting mixture was then warmed to room temperature and then stirred for 2 h. At this time, the reaction was partioned between ethyl acetate and water. The water layer was made acidic with 1N aqueous hydrochloric acid (pH=1). The organic phase was separated and concentrated in vacuo. The residue was dissolved in a small volume of tetrahydrofuran and the mixture was treated with an excess of hexanes. This resulted in the precipitation of the product 4-(2-hydroxy-2-methyl-propyl)-phenol (0.85 g, 77%) as a white solid.

Aufarbeitung

  1. customThe organic phase was separated
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in a small volume of tetrahydrofuran
  4. additionthe mixture was treated with an excess of hexanes

Quellen und Nachweise

ORD-Eintrag
ord-ec8ba2c472af48de883088e447b5e0af
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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