Acetyl chloride → 3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl methyl ketone

HRID 373546Notes

Reaction equation

HRID 373546 reaction equation
[CH3:1][C:2]1([CH3:13])[CH2:8][S:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[S:4][CH2:3]1.[C:14](Cl)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)CCl>[CH3:15][C:14]([C:10]1[CH:11]=[CH:12][C:5]2[S:4][CH2:3][C:2]([CH3:13])([CH3:1])[CH2:8][S:7][C:6]=2[CH:9]=1)=[O:16]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 199355093,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepine

Product 1

HCID 199355193,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl methyl ketone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

13.3 g of 3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepine were dissolved in 110 ml of ethylene chloride under argon and treated portionwise at -10° C. in succession with 10.1 ml of acetyl chloride and 19 g of aluminum chloride. Thereafter, the reaction mixture was stirred at room temperature for 21/2 hours, poured on to ice and extracted with ether. The extract was washed with dilute sodium hydroxide solution and water, dried and evaporated to dryness. There were obtained 15.5 g of 3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepin-7-yl methyl ketone in the form of brownish crystals.

Workup

  1. additionpoured on to ice
  2. extractionextracted with ether
  3. washThe extract was washed with dilute sodium hydroxide solution and water
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-edb055f927854867a2e22ea34620be27
Source dataset
uspto-grants-1992_11
Patent number
US05164387

Reaction notes

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