Hydrochloric Acid → 1-(3-Hydroxyphenyl)-oct-1-yne

HRID 256001

Reaktionsgleichung

Reaktionsgleichung von HRID 256001
C[O:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:7][CH:8]=1.[I-].[Li+].O.Cl>N1C(C)=CC(C)=CC=1C>[OH:2][C:3]1[CH:4]=[C:5]([C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 66321Lithium iodideHCID 112644061-Methoxy-3-(1-octynyl)benzene

Produkt 1

HCID 135002601-(3-Hydroxyphenyl)-oct-1-yne

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 79532,4,6-TrimethylpyridineLösungsmittel

Versuchsvorschrift

1-(3-Methoxyphenyl)-oct-1-yne, (6.50 g, 0.03M), was dissolved in 2,4,6-collidine, (100 ml), and anhydrous lithium iodide (20.08 g, 0.15M), added. The reaction was stirred under nitrogen at reflux temperature for 48 h, then cooled and poured intro water, (500 ml), and acidified with dilute hydrochloric acid. The product was extracted into ethyl acetate, (twice), and the organic phases combined, washed with water (twice) and dried, (MgSO4). Evaporation of the solvent in vacuo yielded the crude product as a brown oil, which was purified by chromatography on silica gel, eluting with dichloromethane/n-hexane [1:1] to chloroform. 5.40 g (90%) of product was collected as a colourless oil. νmax (film) 1580, 1590, 1605, 2230 (weak) 3400 cm-1 ; δ(CDCl3) 0.85 (3H, distorted t, terminal CH3), 1.39 (8H, m, alkylene chain), 2.32 (2H, t, J 6 Hz, acetylenic CH2), 4.77 (1H, s, OH, exchanged with D2O), 6.78 (2H, m, aromatics), 7.02 (2H, m, aromatics).

Aufarbeitung

  1. temperatureat reflux temperature for 48 h
  2. temperaturecooled
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed with water (twice) and
  5. customdried
  6. customEvaporation of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-262448fd7514495bb44c9f9b3a4dd240
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699995

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