Hydrochloric Acid → HCID 10562355, compound

HRID 517625

Reaction equation

HRID 517625 reaction equation
[CH3:1][C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16](Cl)(=[O:20])[C:17](Cl)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(=S)=S>[CH3:1][C:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[C:9]2=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[C:11]3[C:16](=[O:20])[C:17]2=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 130689-MethylanthraceneHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 10562355HCID 10562355, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent2×

Procedure

To a cold (−10° C., brine/ice cooling bath) stirred mixture of 5.43 g (28.2 mmol) of 9-methylanthracene and oxalyl chloride (13.50 mL, 159.5 mmol) in CS2 (60 mL) was added aluminium chloride (6.0 g, 45 mmol). The solution changed from a red-orange colour to a very intense dark crimson colour and vigorous effervescence was observed (hydrogen chloride) and an exotherm occurred raising the reaction temperature from −10° C. to −4° C. After a few minutes stirring the exotherm eased off and an intense dark red tar deposited from the solution which lightened to a yellow colour, the reaction mixture was then stirred cold for a period of 2 hours. After 2 hours, additional CS2 (60 mL) and aluminium chloride (4.5 g, 33.7 mmol) were added, and stirring was continued for 2 hours at 0° C. and then overnight at room temperature. HCl (2M, aq, 150 mL) was then added to the reaction mixture [NOTE: Extreme caution, very exothermic reaction ensues that causes vigorous reflux of reaction solvent], the reaction mixture was then stirred vigorously for 2 hours (large egg-shaped magnetic stirrer follower stirred at 1250 rpm) to decompose the dark red tar to an orange precipitate which was then collected by filtration, washed with water (2×150 mL), and then digested well with 300 mL of 5% NaOH(aq) for a period of 1 hour. The insoluble solids were collected by filtration, washed with water (2×50 mL), and dried in vacuo in a vacuum oven (oil immersion pump) to constant mass (22 hours). Yield: 2.411 g (34.7%, pale orange powder).

Workup

  1. temperaturean exotherm occurred raising the reaction temperature from −10° C. to −4° C
  2. stirringthe reaction mixture was then stirred cold for a period of 2 hours
  3. stirringstirring
  4. waitwas continued for 2 hours at 0° C.
  5. customovernight
  6. customat room temperature
  7. customExtreme caution, very exothermic reaction
  8. temperaturethat causes vigorous reflux of reaction solvent], the reaction mixture
  9. stirringwas then stirred vigorously for 2 hours
  10. stirring(large egg-shaped magnetic stirrer follower stirred at 1250 rpm)
  11. filtrationwas then collected by filtration
  12. washwashed with water (2×150 mL)
  13. waitdigested well with 300 mL of 5% NaOH(aq) for a period of 1 hour
  14. filtrationThe insoluble solids were collected by filtration
  15. washwashed with water (2×50 mL)
  16. customdried in vacuo in a vacuum oven (oil immersion pump) to constant mass (22 hours)

Sources & evidence

ORD record
ord-ca5573fd7e8f4ff98dd89c706f970baa
Source dataset
uspto-grants-2015_08
Patent number
US09115063B2

Linked notes

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