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p-Anisoyl chloride → HCID 15406407, compound

HRID 616631
Notes
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Reaction equation

HRID 616631 reaction equation
[C:1]1([C:7]2[C:11]3[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:10]=3[S:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([C:8]2[S:9][C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=3[C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:25])=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 15422638HCID 15422638, compound

Product 1

HCID 15406407HCID 15406407, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 500 ml. of 1,2-dichloroethane were added 24.0 g. (0.10 mole) of 3-phenyl-6-methoxybenzothiophene and 17.1 g. (0.10 mole) of p-methoxybenzoyl chloride. The mixture was cooled to 0° C., and 13.4 g. (0.10 mole) of aluminum chloride were added. The mixture was stirred for 1 hour, and ice then was added to the mixture. The organic layer was separated, washed with water, and evaporated. To the residue were added a mixture of methanol and 5N sodium hydroxide. The mixture was refluxed for 30 minutes and evaporated. To the residue were added ether and water. The ether layer was separated, washed with 1N sodium hydroxide, 1N hydrochloric acid, and aqueous sodium chloride solution. The ether layer then was dried over magnesium sulfate, filtered, and evaporated to give crude product which was recrystallized from methanol to obtain 34.2 g. (91 percent) of the title compound, m.p. 127°-128° C.

Workup

  1. additionice then was added to the mixture
  2. customThe organic layer was separated
  3. washwashed with water
  4. customevaporated
  5. additionTo the residue were added
  6. additiona mixture of methanol and 5N sodium hydroxide
  7. temperatureThe mixture was refluxed for 30 minutes
  8. customevaporated
  9. additionTo the residue were added ether and water
  10. customThe ether layer was separated
  11. washwashed with 1N sodium hydroxide, 1N hydrochloric acid, and aqueous sodium chloride solution
  12. dry with materialThe ether layer then was dried over magnesium sulfate
  13. filtrationfiltered
  14. customevaporated
  15. customto give crude product which
  16. customwas recrystallized from methanol
  17. customto obtain 34.2 g

Sources & evidence

ORD record
ord-c17227aac2f34e1096c14e077ce01212
Source dataset
uspto-grants-1978_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04075227

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes