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

HRID 1242675Notes

Reaction equation

HRID 1242675 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-].[Cl-].[Cl-].[Al+3].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

Succinic anhydride (17 g, 170 mmol) is added to a solution of thioanisole (20 ml, 170 mmol) in 140 ml of tetrachloroethane and the reaction mixture is then brought to 0° C. Aluminium trichloride (45.43 g, 341 mmol) is added in portions and the reaction mixture is then heated at 60° C. for 3.00 hours. After cooling and hydrolysis in the presence of ice-cold water (500 ml) and concentrated hydrochloric acid (50 ml), the white precipitate formed is filtered off, rinsed with water and recrystallised from ethyl acetate to yield the desired acid.

Workup

  1. customis then brought to 0° C
  2. temperatureAfter cooling
  3. customthe white precipitate formed
  4. filtrationis filtered off
  5. washrinsed with water
  6. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d5d0787678e54e1b8c7b91a717df1b50
Source dataset
uspto-grants-2006_10
Patent number
US07115752B2

Reaction notes

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