Hydrochloric Acid → 4-[2-(Dimethylamino)ethoxy]phenol

HRID 133772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133772
C([O:8][C:9]1[CH:20]=[CH:19][C:12]([O:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[CH:11][CH:10]=1)C1C=CC=CC=1.Cl>C(O)C>[CH3:17][N:16]([CH3:18])[CH2:15][CH2:14][O:13][C:12]1[CH:19]=[CH:20][C:9]([OH:8])=[CH:10][CH:11]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59447665[2-(4-Benzyloxyphenoxy)ethyl]dimethylamine

Produkt 1

HCID 135762384-[2-(Dimethylamino)ethoxy]phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred solution of [2-(4-benzyloxyphenoxy)ethyl]dimethylamine (3.36 g, 0.01238 mol) in the mixture of 6 M HCl (67 ml) and ethanol (33.5 ml) was refluxed for 6.5 h. Then ethanol was evaporated and pH was adjusted to 8 with 2.5 M NaOH. The product was extracted into ethyl acetate. The extracts were washed with water and dried over Na2SO4. Removal of solvent under reduced pressure gave a raw product which was purified by flash chromatography on silica gel using heptane/ethyl acetate (9:1-6:4) as a gradient eluent. 1H NMR (300 MHz, DMSO-d6): 2.20 (6H, s), 2.57 (2H, t, 3J=5.9 Hz), 3.92 (2H, t, 3J=5.9 Hz), 6.65 (2H, d, 3J=9.1 Hz), 6.74 (2H, d, 3J=9.0 Hz), 8.85 (1H, s, —OH).

Aufarbeitung

  1. temperaturewas refluxed for 6.5 h
  2. customThen ethanol was evaporated
  3. extractionThe product was extracted into ethyl acetate
  4. washThe extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-20d584791a364af6bb5b4b90b1b9dbdd
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390923B2

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