Hydrochloric Acid → HCID 14835692, compound

HRID 1709249Notes

Reaction equation

HRID 1709249 reaction equation
N[C:2]1[CH:3]=[C:4](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9].[ClH:18].N([O-])=O.[Na+].C(OCC)(=O)C>C(O)(=O)C>[Cl:18][C:2]1[CH:3]=[C:4](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:5]=[CH:6][C:7]=1[CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 14835691HCID 14835691, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14835692HCID 14835692, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.67 g of ethyl (E)-3-(3-amino-4-isopropylphenyl)acrylate was dissolved in 46.7 ml of acetic acid. To the solution was added 46.7 ml of 2N hydrochloric acid with ice-cooling. To the mixture was dropwise added 10 ml of an aqueous solution containing 1.52 g of sodium nitrite. The mixture was stirred for 30 minutes at the same temperature. The reaction mixture was added to 30 ml of 6N hydrochloric acid solution containing 2.18 g of cuprous chloride, with ice-cooling. The mixture was stirred for 1 hour at the same temperature and then for 2 hours at room temperature. To the reaction mixture was added 100 ml of ethyl acetate. The organic layer was separated and washed with water. Thereto was added 50 ml of water. The mixture was adjusted to about pH 7 with sodium hydrogencarbonate. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=20/1) to obtain 3.57 g of colorless oily ethyl (E)-3-(3-chloro-4-isopropylphenyl)acrylate.

Workup

  1. temperaturecooling
  2. temperaturewith ice-cooling
  3. stirringThe mixture was stirred for 1 hour at the same temperature
  4. waitfor 2 hours at room temperature
  5. customThe organic layer was separated
  6. washwashed with water
  7. additionThereto was added 50 ml of water
  8. customThe organic layer was separated
  9. washwashed with water
  10. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  11. customThe solvent was removed by distillation under reduced pressure
  12. customThe residue was purified by a column chromatography (eluant: n-hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-2b923bc737234e6b93247b22e82d6786
Source dataset
uspto-grants-1990_08
Patent number
US04948796

Reaction notes

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