Hydrochloric Acid → 3,5-Didodecylthio-2-nitrobenzoic acid

HRID 1856131

Reaktionsgleichung

Reaktionsgleichung von HRID 1856131
Cl[C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[C:9](Cl)[CH:10]=1)[C:5]([OH:7])=[O:6].[CH2:15]([SH:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(=O)([O-])[O-].[K+].[K+].Cl>C(O)C.O>[CH2:15]([S:27][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[C:9]([S:27][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:10]=1)[C:5]([OH:7])=[O:6])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 81951-DodecanethiolHCID 11430Potassium CarbonateHCID 52108523,5-Dichloro-2-nitrobenzoic acid

Produkt 1

HCID 233458853,5-Didodecylthio-2-nitrobenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

An amount of 236 g. (1 mole) 3,5-dichloro-2-nitrobenzoic acid (Step 1) and 424 g. (2.1 moles) 1-dodecanethiol in 1.5 liter ethanol and 1 liter water was purged with nitrogen for 15-30 min. Then 430 g. (3.1 moles) anhydrous potassium carbonate were added and the reaction mixture was refluxed under an atmosphere of nitrogen for 60-72 hr. After cooling to room temperature, the solution was poured slowly into a rapidly stirred mixture of 6 liters water, 360 ml. conc. HCl and crushed ice. The precipitated solid was collected and washed well with water. The yellow material was slurried in 2.7 liters of glacial acetic acid, filtered, washed with a small amount of glacial acetic acid and dried in vacuo at 45° C. An amount of 560 g. of the product was obtained, m.p. 74°-77° C.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed under an atmosphere of nitrogen for 60-72 hr
  2. customThe precipitated solid was collected
  3. washwashed well with water
  4. filtrationfiltered
  5. washwashed with a small amount of glacial acetic acid
  6. customdried in vacuo at 45° C
  7. customof the product was obtained

Quellen und Nachweise

ORD-Eintrag
ord-cd4ee0e9c881425993c38534e6a72dce
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04218368

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