Acetyl chloride → HCID 23450668, compound

HRID 964381Notes

Reaction equation

HRID 964381 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]([CH3:20])=[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]([CH3:20])[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 23450716HCID 23450716, compound

Product 1

HCID 23450668HCID 23450668, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

3.2 Grams (24 mmol) of anhydrous aluminum chloride was suspended in 20 ml of methylene chloride, and a solution of 1.9 g (24 mmol) of acetyl chloride in 10 ml of methylene chloride was dropwise added with cooling with ice. The mixture was stirred until the reaction mixture was homogeneous, and a solution of 4.5 g (20 mmol) of 5-chloro-4,4,8-trimethylthiochroman in 10 ml of methylene chloride was added. 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 3.0 g (yield 56%) of 6-acetyl-5-chloro-4,4,8-trimethylthiochroman.

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-7466551e12334296ab8b514e3436d82f
Source dataset
uspto-grants-1998_06
Patent number
US05767289

Reaction notes

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