Hydrochloric Acid → 5-Chloro-2-methoxybenzenebutanoic acid

HRID 2074012Notes

Reaction equation

HRID 2074012 reaction equation
O=[C:2]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C1(C)C=CC=CC=1.Cl>O.[Zn]>[C:5]([CH2:4][CH2:3][CH2:2][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 1140TolueneHCID 64970694-(5-Chloro-2-methoxy-phenyl)-4-oxo-butyric acid

Product 1

HCID 124102565-Chloro-2-methoxybenzenebutanoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

The acid compound of step 1 above is added to a stirring mixture of toluene (22 ml), conc HCl (41 ml), water (17 ml) and the recovered product of mossy zinc (22.2 g) and mercuric chloride (2.2 g) stirred in an aqueous HCl solution for about 10 minutes. The mixture is stirred under reflux for about 16 hours, diluted with water, extracted with ethyl acetate and the organic layer is dried filtered and evaporated. The residue is taken up in 10% aqueous NaOH, and dimethyl sulfate (about 25 ml) added to the mixture which is heated to 80° C. The mixture is stirred at a constant temperature for about 4 hours, cooled, acidified and the resulting precipitate is filtered dried and used in the next step.

Workup

  1. temperatureunder reflux for about 16 hours
  2. extractionextracted with ethyl acetate
  3. customthe organic layer is dried
  4. filtrationfiltered
  5. customevaporated
  6. additiondimethyl sulfate (about 25 ml) added to the mixture which
  7. stirringThe mixture is stirred at a constant temperature for about 4 hours
  8. temperaturecooled
  9. filtrationthe resulting precipitate is filtered
  10. customdried

Sources & evidence

ORD record
ord-bf3bf98523004f5ab8749e5ca4dad799
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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