Hydrochloric Acid → 4-[4-(methylthio)phenyl]-4-oxobutanoic acid

HRID 985774Notes

Reaction equation

HRID 985774 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]1([S:14][CH3:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCC(Cl)(Cl)Cl>[CH3:15][S:14][C:8]1[CH:13]=[CH:12][C:11]([C:1](=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7520ThioanisoleHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 20637154-[4-(methylthio)phenyl]-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

In a 500 ml flask with a ground neck, 0.17 mol of succinic anhydride is added to a solution of 0.17 mol of thioanisole in 140 ml of tetrachloroethane. The mixture is cooled with the aid of an ice bath, and 0.34 mol of aluminium chloride is added in small portions. The mixture is then heated at 60° C. for 3 hours. The reaction mixture is then cooled, poured into ice-cold water and acidified with 3M HCl solution. The precipitate formed is filtered off under suction, washed with cyclohexane and recrystallised.

Workup

  1. temperatureThe mixture is cooled with the aid of an ice bath
  2. temperatureThe reaction mixture is then cooled
  3. additionpoured into ice-cold water
  4. customThe precipitate formed
  5. filtrationis filtered off under suction
  6. washwashed with cyclohexane
  7. customrecrystallised

Sources & evidence

ORD record
ord-f6209df712a341dfa83f081a36ad1fd6
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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