Ammonium Chloride → 3-(2,3-Dichlorophenyl)propanoic acid

HRID 1253798Notes

Reaction equation

HRID 1253798 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[Mg].[Cl-].[NH4+]>CO>[Cl:1][C:2]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27347623-(2,3-dichlorophenyl)prop-2-enoic AcidHCID 5462224Magnesium

Product 1

HCID 125951013-(2,3-Dichlorophenyl)propanoic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,3-dichlorocinnamic acid (1.0 g) in methanol (50 mL), magnesium (1.34 g) was added under ice-cooling and the resultant reaction mixture was stirred at room temperature for 3 days. To the reaction mixture, a saturated ammonium chloride aqueous solution was added and the resultant reaction mixture was extracted with dichloromethane. The organic phase was washed with a saturated saline and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure to obtain the subject compound (912 mg) as a white solid.

Workup

  1. temperaturecooling
  2. customthe resultant reaction mixture
  3. customthe resultant reaction mixture
  4. extractionwas extracted with dichloromethane
  5. washThe organic phase was washed with a saturated saline
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationFrom the organic phase, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2b0f57a98f1d47ebb7be6c078797aa75
Source dataset
uspto-grants-2013_06
Patent number
US08455500B2

Reaction notes

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