Hydrochloric Acid → 4-(5-Chloro-2-methoxy-phenyl)-4-oxo-butyric acid

HRID 2074011Notes

Reaction equation

HRID 2074011 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClC(Cl)=C(Cl)Cl.[N+](C1C=CC=CC=1)([O-])=O>[O:16]=[C:10]([C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:8][CH3:9])[CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 121674-ChloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 64970694-(5-Chloro-2-methoxy-phenyl)-4-oxo-butyric acid

Reagents, catalysts & solvents 1

HCID 86743877HCID 86743877, compoundSolvent

Procedure

A mixture of 4-chloroanisole (20 g), succinic anhydride (16 g) and AlCl3 (42 g) in 1:1 tetrachloroethylene/nitrobenzene (200 ml) is stirred at -10°-0° C. for a week. The mixture is poured into a conc. HCl/crushed ice bath and the solvent is distilled under vacuo at 40° C. The resulting suspension is made basic with 10% aqueous NaHCO3. The solids are filtered and the filtrate made acidic forming a precipitate which is filtered, washed with water, taken up in ethanol and dried. The solution is filtered and evaporated affording the desired product as a white solid, M.P. 113°-115° C.

Workup

  1. customcrushed ice bath
  2. distillationthe solvent is distilled under vacuo at 40° C
  3. filtrationThe solids are filtered
  4. customthe filtrate made acidic forming a precipitate which
  5. filtrationis filtered
  6. washwashed with water
  7. customdried
  8. filtrationThe solution is filtered
  9. customevaporated

Sources & evidence

ORD record
ord-09f515e974bc4e47a978b436d5abc0c5
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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