Hydrochloric Acid → (E)-3-(4-chloro-3-hydroxy-phenyl)-acrylic acid ethyl ester

HRID 1184542Notes

Reaction equation

HRID 1184542 reaction equation
[CH2:1]([O:3][C:4](=[O:15])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10](N)=[C:9]([OH:14])[CH:8]=1)[CH3:2].N([O-])=O.[Na+].[ClH:20]>O.[Cu]Cl>[CH2:1]([O:3][C:4](=[O:15])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([Cl:20])=[C:9]([OH:14])[CH:8]=1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 20258356(E)-3-(4-amino-3-hydroxy-phenyl)-acrylic acid ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 67337784(E)-3-(4-chloro-3-hydroxy-phenyl)-acrylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolvent2×

Procedure

(E)-3-(4-Amino-3-hydroxy-phenyl)-acrylic acid ethyl ester (2.76 g, 13.3 mmol) was suspended in HCl solution (6N, 4 ml), and sodium nitrite solution in water (960 mg, 14 mmol) was added at 0° C. The resulting suspension was added at 0° C. to a solution of copper (I) chloride (2 g, 16 mmol) in concentrated HCl (4 ml). The mixture was slowly warmed to RT and heated to 60° C. for 30 min., shaking occasionally. Then it was cooled to RT, diluted with water and extracted with DCM, which was dried and evaporated. The residue was purified by silica gel column chromatography, eluant petroleum ether/AcOEt 90:10, to give 1.46 g of (E)-3-(4-chloro-3-hydroxy-phenyl)-acrylic acid ethyl ester as a white solid.

Workup

  1. temperatureheated to 60° C. for 30 min.
  2. temperatureThen it was cooled to RT
  3. extractionextracted with DCM, which
  4. customwas dried
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography, eluant petroleum ether/AcOEt 90:10

Sources & evidence

ORD record
ord-ac5ed94a75fe4071b8603f939cf1d784
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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