Chloride → (2-Thienyl) (3,5-dimethyl-4-methoxyphenyl)ketone

HRID 2049301Notes

Reaction equation

HRID 2049301 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[Cl-].[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17](O)=[O:18].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:17]([C:6]1[CH:5]=[C:4]([CH3:8])[C:3]([O:9][CH3:10])=[C:2]([CH3:1])[CH:7]=1)=[O:18]

Participants

7

Reactant 5

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 107002-Thiophenecarboxylic acidHCID 660882,6-DimethylanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57211859(2-Thienyl) (3,5-dimethyl-4-methoxyphenyl)ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

Into a solution of 60 g of 2,6-dimethyl anisole and 62.7 g of the chloride of 2-thiophene carboxylic acid in 250 ml of anhydrous methylene chloride there was introduced over 30 minutes 58.5 g of aluminium chloride while maintaining the temperature at about 10° C. The reaction medium was brought to the reflux temperature of the solvent for 21/2 hours, then poured onto one kg of crushed ice mixed with 150 ml of concentrated hydrochloric acid. The organic phase was decanted, the aqueous phase extracted with methylene chloride, and the organic phase washed with an aqueous solution of sodium hydroxide, then with water. After drying and evaporation of the solvent, 110 g of an oil was isolated which was distilled under reduced pressure to give 89 g of ketone. Boiling point (14 mm Hg)=225° C.

Workup

  1. custom2 hours
  2. customThe organic phase was decanted
  3. extractionthe aqueous phase extracted with methylene chloride
  4. washthe organic phase washed with an aqueous solution of sodium hydroxide
  5. customAfter drying
  6. customevaporation of the solvent

Sources & evidence

ORD record
ord-d8af54cfa41e43adbd02df010a19cc65
Source dataset
uspto-grants-1980_04
Patent number
US04197309

Reaction notes

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