Hydrochloric Acid → HCID 10888856, compound

HRID 566848Notes

Reaction equation

HRID 566848 reaction equation
[Mg].[CH2:2]([C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1)[CH2:3][CH3:4].[C:12](=[S:14])=[S:13].Cl>C1COCC1>[CH2:2]([C:5]1[CH:10]=[CH:9][C:8]([C:12]([SH:14])=[S:13])=[CH:7][CH:6]=1)[CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 1363741-Bromo-4-propylbenzeneHCID 5462224Magnesium

Product 1

HCID 10888856HCID 10888856, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To a 1000 ml three neck flask provided with a stirrer, thermometer, dropping funnel, and nitrogen gas introducing tube were added 9.4 g (386.8 mmol) of magnesium turnings and 20 ml of THF under nitrogen gas atmosphere, and 200 ml solution of 70.0 g (351.6 mmol) of 4-propylbromobenzene in THF was added dropwise while being stirred in 1 hour while the reaction temperature being adjusted at 45 to 55° C. After finishing of the dropping, it was stirred at 55° C. for 2 hours. The reaction mixture thus obtained was cooled down to a temperature lower than 10° C., 133.8 g (1.75 mol) of carbon disulfide was added dropwise thereto in 50 minutes. After finishing of the dropping, it was further stirred at room temperature for 14 hours. The reaction mixture was cooled down to a temperature lower than 5° C., and then 100 ml of 6N hydrochloric acid was added dropwise thereto to terminate the reaction. It was extracted with 300 ml of diethyl ether, and the extract was washed with water (200 ml) thrice, dried over anhydrous magnesium sulfate, and the solvent was distilled off under a reduced pressure to obtain 64.2 g of purplish red oily 4-propyldithiobenzoic acid. 1H-NMR (δ ppm): 0.95 (3H, t, J=7.4 Hz), 1.65 (2H, m), 2.63 (2H, t, J=7.8 Hz), 6.0-6.5 (1H, bs), 7.18 (2H, d, J=8.3 Hz), 7.99 (2H, d, J=8.6 Hz).

Workup

  1. additionnitrogen gas introducing tube
  2. custombeing adjusted at 45 to 55° C
  3. stirringwas stirred at 55° C. for 2 hours
  4. customThe reaction mixture thus obtained
  5. waitin 50 minutes
  6. stirringwas further stirred at room temperature for 14 hours
  7. temperatureThe reaction mixture was cooled down to a temperature lower than 5° C.
  8. customto terminate
  9. customthe reaction
  10. extractionIt was extracted with 300 ml of diethyl ether
  11. washthe extract was washed with water (200 ml) thrice
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationthe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-f1865df0a67a43708622fe642e93879b
Source dataset
uspto-grants-2001_01
Patent number
US06177154B1

Reaction notes

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