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Hydrochloric Acid → Benzene, [[(methylthio)methyl]thio]-

HRID 65810
Notes
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Reaction equation

HRID 65810 reaction equation
C([Li])CCC.[C:6]1([S:12][CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:14][S:15]SC.Cl>CCCCCC.O1CCCC1>[C:6]1([S:12][CH2:13][S:15][CH3:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7520ThioanisoleHCID 12232Dimethyl DisulfideHCID 178418339Butyllithium

Product 1

HCID 11789655Benzene, [[(methylthio)methyl]thio]-

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8058
Hexane
Solvent

Conditions

Temperature
-70 °C

Procedure

120 ml. of a 1.3M n-butyllithium solution in n-hexane were added dropwise to a solution of 18.8 ml. of thioanisole in 240 ml. of tetrahydrofuran at -20° C. and the reaction mixture was stirred at that temperature for 2 hours. After cooling to -70° C., 16.4 g. of dimethyldisulphide were added to the reaction mixture, which was then stirred at -70° C. for 15 minutes and at room temperature for 1 hour. The reaction mixture was poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate. The extracts were washed with water and an aqueous solution of sodium chloride and concentrated under reduced pressure. The residue was purified by distillation in vacuo to give 18.0 g. of the title compound having the following physical characteristics:

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water
  3. concentrationan aqueous solution of sodium chloride and concentrated under reduced pressure
  4. distillationThe residue was purified by distillation in vacuo
  5. customto give 18.0 g

Sources & evidence

ORD record
ord-97b77afb4189423cbe59a6a3ae2f079d
Source dataset
uspto-grants-1978_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04128720

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes