Thionyl Chloride → 5-Chloro-2-methoxybenzoyl chloride

HRID 76245

Reaktionsgleichung

Reaktionsgleichung von HRID 76245
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].O=S(Cl)[Cl:15]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 769705-Chloro-o-anisic acid

Produkt 1

HCID 123841765-Chloro-2-methoxybenzoyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

5-Chloro-2-methoxybenzoic acid (11.3 g, 60.56 mmol) and SOCl2 (9 mL, 123.7 mmol) in toluene (20 mL) were heated gently while vigorous gas evolution occurred. After gas evolution had subsided, the reaction was heated to reflux for 1.5 h, cooled and stirred overnight at room temperature. The volatiles were evaporated in vacuo and the remaining material was treated with toluene and evaporated (2×) to remove excess SOCl2 to provide a white solid that was taken directly on to the next step without purification. 1H NMR (300 MHz, CDCl3) δ 3.92 (s, 3H), 6.95 (d, 1H), 7.53 (dd, 1H), 8.03 (d, 1H).

Aufarbeitung

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1.5 h
  3. temperaturecooled
  4. customThe volatiles were evaporated in vacuo
  5. additionthe remaining material was treated with toluene
  6. customevaporated (2×)
  7. customto remove excess SOCl2
  8. customto provide a white solid that
  9. customwas taken directly on to the next step without purification

Quellen und Nachweise

ORD-Eintrag
ord-7d6c7a2dd55e4ebe90303567f09ff2a2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835475B2

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