Hydrochloric Acid → 1,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)

HRID 1521799Notes

Reaction equation

HRID 1521799 reaction equation
[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[CH:13][CH:12]=3.[Al+3].[Cl-].[Cl-].[Cl-].[C:21](Cl)(=[O:23])[CH3:22].Cl>C(Cl)Cl>[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:21](=[O:23])[CH3:22])[CH:12]=3

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 123269761-(4,5-Dihydronaphtho[1,2-b]thiophen-2-yl)ethan-1-one

Product 1

HCID 123269771,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)Yield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4,5-dihydronaphtho[1,2-b]thiophen-2-yl)ethanone (5b) (30 g, 131 mmol) in 500 mL of DCM at 0° C., AlCl3 (52.6 g, 394 mmol) was added portion wise and after 15 min, acetyl chloride (18.69 ml, 263 mmol) was added dropwise at the same temperature over 30 min and the mixture was stirred at room temperature for 48 hr. The reaction mass was slowly added to ice water and acidified with 2 N HCl solution and extracted with DCM, and the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound as an yellow solid (5c) (28.3 g, 80%). m/z 270.0 (M+).

Workup

  1. extractionextracted with DCM
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-220c41444cac477eb4ec9c7ba1697021
Source dataset
uspto-grants-2015_07
Patent number
US09073942B2

Reaction notes

Loading…