Hydrochloric Acid → HCID 54221571, compound

HRID 1679509Notes

Reaction equation

HRID 1679509 reaction equation
[C:1]([C:9]([O:12][C:13]1[CH:19]=[CH:18][C:16](N)=[CH:15][CH:14]=1)([CH3:11])[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:20].N([O-])=O.[Na+].[OH2:25]>CC(C)=O.C(O)(=O)C=C>[Cl:20][CH:2]([CH2:3][C:16]1[CH:18]=[CH:19][C:13]([O:12][C:9]([C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([CH3:11])[CH3:10])=[CH:14][CH:15]=1)[C:1]([OH:8])=[O:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 20363173HCID 20363173, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 54221571HCID 54221571, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6581Acrylic AcidSolvent

Procedure

In 30 ml of acetone is dissolved 2.6 g of 4-(2-benzoyl-2-propyloxy)aniline and, under cooling with ice and stirring, 3.5 ml of hydrochloric acid, a solution of 0.8 g sodium nitrite in 3 ml water, 7 ml of acrylic acid and 0.7 g of finely divided cuprous chloride are added in the order mentioned. The mixture is stirred at 35° C for 1 hour and at room temperature for 1 hour, after which it is extracted with benzene. The extract is washed three times with water, and then the solvent is distilled off. The residue is dissolved in 10% of aqueous sodium bicarbonate, the solution is washed with benzene and then acidified with hydrochloric acid. The resultant oily substance is extracted with ether and the ether is distilled off to give 2 g of 2-chloro-3-[4-(2-benzoyl-2-propyloxy)phenyl]-propionic acid as a yellow oily substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture is stirred at 35° C for 1 hour and at room temperature for 1 hour
  3. extractionafter which it is extracted with benzene
  4. washThe extract is washed three times with water
  5. distillationthe solvent is distilled off
  6. dissolutionThe residue is dissolved in 10% of aqueous sodium bicarbonate
  7. washthe solution is washed with benzene
  8. extractionThe resultant oily substance is extracted with ether
  9. distillationthe ether is distilled off

Sources & evidence

ORD record
ord-bd42dcb55d72403084cfdc6e08413b71
Source dataset
uspto-grants-1978_03
Patent number
US04080505

Reaction notes

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