Acetone → Ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propanoate

HRID 1679506Notes

Reaction equation

HRID 1679506 reaction equation
[CH3:1][C:2]([CH3:18])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8](N)=[CH:7][CH:6]=1.[ClH:19].N([O-])=O.[Na+].C[C:25]([CH3:27])=[O:26]>O.C(OCC)(=O)C=C>[Cl:19][CH:2]([CH2:1][C:8]1[CH:10]=[CH:11][C:5]([O:4][CH2:3][C:2]([CH3:18])([CH3:1])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:7]=1)[C:3]([O:26][CH2:25][CH3:27])=[O:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 126340334-(2-Methyl-2-phenylpropoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 194150Ethyl 2-chloro-3-[4-(2-methyl-2-phenylpropoxy)phenyl]propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8821Ethyl AcrylateSolvent

Procedure

In 150 ml of acetone is dissolved 16.8 g of 4-(2,2-dimethyl-2-phenylethyloxy)aniline and, under cooling with ice and stirring, 20 ml of hydrochloric acid, a solution of 6 g sodium nitrite in 20 ml water, 75 ml of ethyl acrylate and 0.3 g of finely divided cuprous oxide are added in the order mentioned. The mixture is stirred at 10° C for 30 minutes and at room temperature for 2 hours. After the reaction has been completed, the reaction mixture is concentrated under reduced pressure and extracted with ether. The ether is distilled off and residual oil is purified by chromatography on silica gel. The described procedure yields 17.7 g of ethyl 2-chloro-3-[4-(2,2-dimethyl-2-phenylethyloxy)phenyl]propionate as a yellowish oily product. Cyclohexane/benzene is used as the eluant solvent (1:1). Boiling point: 205°-206° C/0.9 mmHg

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture is stirred at 10° C for 30 minutes and at room temperature for 2 hours
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. extractionextracted with ether
  5. distillationThe ether is distilled off
  6. customresidual oil is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f3fd9668e9e244ae94445b21e7583eb1
Source dataset
uspto-grants-1978_03
Patent number
US04080505

Reaction notes

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