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

HRID 1390523Notes

Reaction equation

HRID 1390523 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 233458853,5-Didodecylthio-2-nitrobenzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3fd56e7c8f914fdc83d332cd6f7a1de4
Source dataset
uspto-grants-1979_02
Patent number
US04139379

Reaction notes

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