Acetyl chloride → 1-(4,4-Dimethylthiochroman-6-yl)ethanone

HRID 2232467Notes

Reaction equation

HRID 2232467 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[CH3:9][C:10]1([CH3:20])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[S:13][CH2:12][CH2:11]1>C(Cl)Cl>[CH3:6][C:5]([C:17]1[CH:18]=[CH:19][C:14]2[S:13][CH2:12][CH2:11][C:10]([CH3:9])([CH3:20])[C:15]=2[CH:16]=1)=[O:7]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 110194304,4-Dimethylthiochroman

Product 1

HCID 117083551-(4,4-Dimethylthiochroman-6-yl)ethanoneYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

37 g of aluminum chloride were suspended at 0° C. in 200 ml of methylene chloride and the suspension was treated slowly with 22 g of acetyl chloride while stirring vigorously. After 30 minutes, a solution of 49.4 g of 3,4-dihydro-4,4-dimethyl 2H-1-benzothiopyran in 150 ml of methylene chloride was added dropwise thereto. After stirring at 0° C. for 1 hour, the mixture was poured into ice/water and extracted with methylene chloride. The organic phase was washed neutral with 1N sodium hydroxide solution and water, dried and evaporated. The oily crude product was filtered over a short column of silica gel [eluting agent: hexane/ether (9:1)]. There were obtained 51.5 g of 3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl methyl ketone in the form of a colorless oil which solidifies upon standing in a refrigerator.

Workup

  1. stirringAfter stirring at 0° C. for 1 hour
  2. extractionextracted with methylene chloride
  3. washThe organic phase was washed neutral with 1N sodium hydroxide solution and water
  4. customdried
  5. customevaporated
  6. filtrationThe oily crude product was filtered over a short column of silica gel [eluting agent: hexane/ether (9:1)]

Sources & evidence

ORD record
ord-b8121998248449fb9d40e902c614d832
Source dataset
uspto-grants-1988_11
Patent number
US04788213

Reaction notes

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