Acetyl chloride → HCID 22118452, compound

HRID 1275476Notes

Reaction equation

HRID 1275476 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[CH:11][C:12]=2[CH3:14])[S:7][CH2:6][CH2:5]1.[Cl-].[Al+3].[Cl-].[Cl-].[C:20](Cl)(=[O:22])[CH3:21]>ClC(Cl)C>[C:20]([C:11]1[C:12]([CH3:14])=[C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=1)[S:7][CH2:6][CH2:5][CH:4]2[CH2:3][O:2][CH3:1])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 22118423HCID 22118423, compound

Product 1

HCID 22118452HCID 22118452, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 0.84 g (3.78 mmol) of 4-methoxymethyl-5,8-dimethylthiochroman and 0.60 g (4.54 mmol) of aluminum chloride in dichloroethane was dropwise added 0.36 g (4.54 mmol) of acetyl chloride at 0° C., and the mixture was further allowed to react at 0° C. for 1 hour. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution, and an organic layer was dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure to give 0.30 g (yield 30%) of the titled compound as a crude product.

Workup

  1. customat 0° C.
  2. customto react at 0° C. for 1 hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated sodium chloride aqueous solution
  5. dry with materialan organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3a6c5dd6a182490eb7f04c6374fbfc2c
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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