Hydrochloric Acid → Ethyl 2-chloro-3-(3,4-diethoxyphenyl)propionate

HRID 354683Notes

Reaction equation

HRID 354683 reaction equation
C([C:4]([Cl:23])([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([O:20][CH2:21][CH3:22])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)C.[OH-].[Ba+2].[OH-].Cl>C(O)C>[Cl:23][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[C:13]([O:20][CH2:21][CH3:22])[CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6093286Barium hydroxideHCID 13103719Ethyl 2-acetyl-2-chloro-3-(3,4-diethoxyphenyl)propionate

Product 1

HCID 13103729Ethyl 2-chloro-3-(3,4-diethoxyphenyl)propionateYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 150 ml of ethanol is dissolved 14.0 g of the above ethyl 2-acetyl-2-chloro-3-(3,4-diethoxyphenyl)propionate, followed by addition of 3.5 g of anhydrous barium hydroxide. The mixture is stirred under ice cooling for 30 minutes, then poured into 300 g ice-40 ml 6N-HCl, and extracted with ether. The ethereal layer is washed with water, dried (over MgSO4) and distilled to remove the ether. The above procedure provides 12.0 g (97.6%) of ethyl 2-chloro-3-(3,4-diethoxyphenyl)propionate as oil.

Workup

  1. extractionextracted with ether
  2. washThe ethereal layer is washed with water
  3. dry with materialdried (over MgSO4)
  4. distillationdistilled
  5. customto remove the ether

Sources & evidence

ORD record
ord-92e42c34128247a5b65f559681315c64
Source dataset
uspto-grants-1983_03
Patent number
US04376777

Reaction notes

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