Acetyl chloride → HCID 23450706, compound

HRID 1839872Notes

Reaction equation

HRID 1839872 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[Cl:9][C:10]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]2[C:11]=1[C:12]([CH3:22])([CH3:21])[CH2:13][CH2:14][S:15]2>C(Cl)Cl>[C:5]([C:19]1[C:10]([Cl:9])=[C:11]2[C:16](=[C:17]([Cl:20])[CH:18]=1)[S:15][CH2:14][CH2:13][C:12]2([CH3:22])[CH3:21])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 23450686HCID 23450686, compound

Product 1

HCID 23450706HCID 23450706, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.26 Grams (9.45 mmol) of anhydrous aluminum chloride was suspended in 10 ml of methylene chloride, and a solution of 0.74 g (9.45 mmol) of acetyl chloride in 5 ml of methylene chloride was dropwise added with cooling with ice. The mixture was stirred until the reaction mixture was homogeneous, then, a solution of 1.95 g (7.88 mmol) of 5,8-dichloro-4,4-dimethylthiochroman in 5 ml of methylene chloride was added, and the mixture was allowed to react at room temperature for 1 hour. After the completion of the reaction, the reaction mixture was poured into ice water and extracted with methylene chloride. An organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The methylene chloride was distilled off under reduced pressure, and the resultant oily substance was purified by silica gel column chromatography to give 1.27 g (yield 56%) of 6-acetyl-5,8-dichloro-4,4-dimethylthiochroman.

Workup

  1. temperaturewith cooling with ice
  2. customto react at room temperature for 1 hour
  3. customAfter the completion of the reaction
  4. extractionextracted with methylene chloride
  5. washAn organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe methylene chloride was distilled off under reduced pressure
  8. customthe resultant oily substance was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-dc6095ce74d841e99620ffcca85d3a90
Source dataset
uspto-grants-2004_01
Patent number
US06677460B1

Reaction notes

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