Hydrochloric Acid → 1-Propanone, 1-(2,3-dihydro-2-methylbenzo[b]thien-5-yl)-

HRID 980501Notes

Reaction equation

HRID 980501 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[CH3:10][CH:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[CH2:12]1.Cl>ClC=CCl>[C:5]([C:18]1[CH:17]=[CH:16][C:14]2[S:15][CH:11]([CH3:10])[CH2:12][C:13]=2[CH:19]=1)(=[O:8])[CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12204680Benzo[b]thiophene, dihydromethyl-

Product 1

HCID 122561351-Propanone, 1-(2,3-dihydro-2-methylbenzo[b]thien-5-yl)-

Reagents, catalysts & solvents 1

HCID 109001,2-DichloroethyleneSolvent

Conditions

Temperature
10 °C

Procedure

To 0.15M of aluminum chloride, 0.11M of propionyl chloride and 150 ml of 1,2-dichloroethylene, 0.1M of 2-methyl2,3-dihydrobenzo[b]-thiophene (prepared according to method of Petropoulos, J. Am. Chem. Soc., 75, 1130, 1953) are added slowly, temperature being maintained at ±10° C. After addition, the mixture is still stirred for 3 hours at room temperature, then a mixture of ice and HCl is added. The mixture is extracted with 1,2-dichloroethylene, dried on MgSO4 and solvent is evaporated. The oily residue as stripped in vacuum. 14 gr. of 5-propionyl-2-methyl-2,3-dihydrobenzo[b]thiophene are so obtained.

Workup

  1. additionAfter addition
  2. additionis added
  3. extractionThe mixture is extracted with 1,2-dichloroethylene
  4. customdried on MgSO4 and solvent
  5. customis evaporated

Sources & evidence

ORD record
ord-56883e7ae8fa470a8194ddd2dfeda2a8
Source dataset
uspto-grants-1987_01
Patent number
US04638070

Reaction notes

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