Hydrochloric Acid → 1-(Dibenzo[b,d]thiophen-2-yl)ethan-1-one
Reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl.[C:19](Cl)(=[O:21])[CH3:20]>C(Cl)(Cl)(Cl)Cl.ClCCl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:19]([CH3:20])=[O:21]Participants
Procedure
To a solution of 147.4 g of dibenzothiophene in 1.6 liters of carbon tetrachloride, cooled in an ice bath, was added a filtered solution of 122.7 g of anhydrous aluminum chloride in 425 ml of dichloromethane and 65.4 ml of acetyl chloride at 10° C., over 45 minutes. The mixture was stirred for 20 minutes, then a mixture of 2.5 liters of crushed ice and 500 ml of concentrated hydrochloric acid was added in one portion. This mixture was stirred vigorously until the yellow color disappeared. The aqueous layer was separated and washed in 100 ml of carbon tetrachloride. The wash was combined with the organic layer, washed with two 2 liter portions of water, dried and evaporated. The residue was crystallized from 250 ml of toluene and 750 ml of ether, giving 85.9 g of the desired product as colorless crystals, mp 107°-110° C.
Workup
- additionwas added in one portion
- stirringThis mixture was stirred vigorously until the yellow color
- customThe aqueous layer was separated
- washwashed in 100 ml of carbon tetrachloride
- washwashed with two 2 liter portions of water
- customdried
- customevaporated
- customThe residue was crystallized from 250 ml of toluene and 750 ml of ether
Sources & evidence
- ORD record
- ord-c6048bc4716741e68ab388f9241e3f78
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04965284
Reaction notes
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