Hydrochloric Acid → 1-(Cyclohex-1-en-1-yl)-3-methoxybenzene

HRID 1837180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1837180
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.O=S(Cl)Cl.N1C=CC=CC=1.Cl>C1COCC1>[C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 146851021-(3-Methoxyphenyl)cyclohexan-1-ol

Produkt 1

HCID 2658181-(Cyclohex-1-en-1-yl)-3-methoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 1L 3-neck RBF under argon was charged with crude 1-(m-methoxyphenyl)cyclohexanol (59.2 g, 287 mmol). To the flask was added 592 mL of dry THF. The reaction was cooled to 0° C., and to it was slowly added SOCl2 (58.6 mL, 803.6 mmol). After stirring for 10 minutes, pyridine (104 mL, 1.29 mol) was added slowly. The reaction mixture stirred slowly at 22° C. for 2 hours, and then it was cooled back to 0° C. 1N HCl (500 mL) was slowly added to the reaction. The layers were separated. The THF layer was dried (MgSO4), filtered, and concentrated in vacuo. The crude product was chromatographed using 100% hexane as eluent to provide 39.5 g (82%, 2 steps) of product. 1H NMR (CDCl3) δ1.72 (m, 2H), 1.83 (m, 2H), 2.24 (m, 2H), 2.45 (m, 2H), 3.86 (s, 3H), 6.18 (m, 1H), 6.83 (dd, J=8.1, 1.7 Hz, 1H), 6.98 (m, 1H), 7.03 (d, J=6.1 Hz, 1H), 7.27 (t, J=7.8 Hz, 1H).

Aufarbeitung

  1. stirringThe reaction mixture stirred slowly at 22° C. for 2 hours
  2. temperatureit was cooled back to 0° C
  3. customThe layers were separated
  4. dry with materialThe THF layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was chromatographed
  8. customto provide 39.5 g (82%, 2 steps) of product

Quellen und Nachweise

ORD-Eintrag
ord-f6061f52c0a1436aa657baa43c306194
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780891B2

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