Sodium Hydroxide → 3-(3,5-Dichlorophenyl)acrylic acid

HRID 1480421Notes

Reaction equation

HRID 1480421 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([O:13]C)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69907122Methyl (E)-3-(3,5-dichlorophenyl)acrylate

Product 1

HCID 64421483-(3,5-Dichlorophenyl)acrylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (E)-methyl 3-(3,5-dichlorophenyl)acrylate (step 1) (2 g, 8.66 mmol) in THF (35 ml) was added 2M NaOH (12.98 ml, 26.0 mmol) and the reaction mixture was stirred at RT overnight. The solvent was removed under reduced pressure and the residue was dissolved in water and washed with EtOAc. The aqueous portion was acidified to pH 4 using 1M HCl and extracted with DCM. The organic portion was dried using a phase separating column and the solvent removed under reduced pressure to afford the title compound as a white solid;

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. washwashed with EtOAc
  4. extractionextracted with DCM
  5. customThe organic portion was dried
  6. customseparating column
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-caab693769ac4e62b8ba72e0eb1f1095
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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