Hydrochloric Acid → HCID 10969180, compound

HRID 1859336Notes

Reaction equation

HRID 1859336 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1.Cl>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:15][S:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22123590Ethyl 2-(4-methoxyphenyl)-3-(3-methoxyphenylthio)propionate

Product 1

HCID 10969180HCID 10969180, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To acetone solution(300 ml) of ethyl 2-(4-methoxyphenyl)-3-(3-methoxyphenylthio)propionate (3) (30.2 g, 87.3 mmol) obtained above was added aqueous 6N--HCl solution (200 ml) and then heated under refluxing for 60 hours. The reaction solution was extracted with ether, and the organic layer was alkalized with aqueous 20% NaOH solution. Then the aqueous layer was separated, acidified with 20% HCl solution and extracted with ether. The ether layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent to obtain 25.4 g (yield: 91%) of 2-(4-methoxyphenyl)-3-(3-methoxyphenylthio)propionic acid (4).

Workup

  1. additionabove was added aqueous 6N
  2. temperatureunder refluxing for 60 hours
  3. extractionThe reaction solution was extracted with ether
  4. customThen the aqueous layer was separated
  5. extractionextracted with ether
  6. washThe ether layer was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent

Sources & evidence

ORD record
ord-ec180fe77c3a400b9557bf1c83b1720f
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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