Hydrochloric Acid → (4-Methoxyphenyl)(3-methoxythiophen-2-yl)methanone

HRID 1445323Notes

Reaction equation

HRID 1445323 reaction equation
[Sn](Cl)(Cl)(Cl)Cl.[CH3:6][O:7][C:8]1[CH:12]=[CH:11][S:10][CH:9]=1.[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.Cl>ClCCl>[CH3:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([C:9]2[S:10][CH:11]=[CH:12][C:8]=2[O:7][CH3:6])=[O:20])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 24287Tin tetrachlorideHCID 1402493-Methoxythiophene

Product 1

HCID 21961240(4-Methoxyphenyl)(3-methoxythiophen-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.7 ml of tin tetrachloride were added to a solution of 2.3 g of 3-methoxy-thiophene and 3.4 g of 4-methoxybenzoyl chloride in 50 ml of dichloromethane while cooling in ice. The mixture was stirred at room temp. overnight. For workup, 75 ml of 2 hydrochloric acid were added and the mixture was extracted three times with dichloromethane. The combined organic phases were washed twice with each of 2 N sodium carbonate solution and water, and then the solvent was removed in vacuo, and the crude product was purified by column filtration (SiO2, ethyl acetate/n-heptane=1:2). The product with the molecular weight of 248.3 (C13H12O3S), MS (Cl): 249 (M+H+) was obtained.

Workup

  1. temperaturewhile cooling in ice
  2. extractionthe mixture was extracted three times with dichloromethane
  3. washThe combined organic phases were washed twice with each of 2 N sodium carbonate solution and water
  4. customthe solvent was removed in vacuo
  5. filtrationthe crude product was purified by column filtration (SiO2, ethyl acetate/n-heptane=1:2)
  6. customThe product with the molecular weight of 248.3 (C13H12O3S), MS (Cl): 249 (M+H+) was obtained

Sources & evidence

ORD record
ord-802e1cc6d523441abf2a7bd184301e8e
Source dataset
uspto-grants-2010_02
Patent number
US07666848B2

Reaction notes

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