Hydrochloric Acid → HCID 21450426, compound

HRID 596635Notes

Reaction equation

HRID 596635 reaction equation
[CH2:1]([SH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[H-].[Na+].Cl[C:17]1[S:21][C:20]([C:22]([OH:24])=[O:23])=[CH:19][CH:18]=1.Cl>C1(C)C=CC=CC=1.O>[CH2:1]([S:13][C:17]1[S:21][C:20]([C:22]([OH:24])=[O:23])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81951-DodecanethiolHCID 24758Sodium hydrideHCID 950485-Chloro-2-thiophenecarboxylic acid

Product 1

HCID 21450426HCID 21450426, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 40.5 g (0.2 mole) of 1-dodecanethiol (laurylmercaptan) in 19.2 g (0.4 mole) of sodium hydride (50% in oil) in 1 liter of toluene is refluxed with stirring for 1 hour then cooled to room temperature. To the mixture 32.5 g (0.2 mole) of 5-chloro-2-thiophenecarboxylic acid is added and the mixture is refluxed with stirring for 24 hours after which the mixture is cooled to room temperature and acidified with 5% aqueous hydrochloric acid. Water is added, and the toluene layer is separated, dried over sodium sulfate and evaporated to give 5-(dodecylthio)-2-thiophenecarboxylic acid.

Workup

  1. temperatureis refluxed
  2. temperaturethe mixture is refluxed
  3. stirringwith stirring for 24 hours after which the mixture
  4. temperatureis cooled to room temperature
  5. customthe toluene layer is separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-3c0172162c4b41449cad64e5846c1373
Source dataset
uspto-grants-1977_03
Patent number
US04011334

Reaction notes

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