Hydrochloric Acid → HCID 13290079, compound

HRID 1903516Notes

Reaction equation

HRID 1903516 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][O:6][C:7]1[C:19]([Cl:20])=[C:18]([Cl:21])[C:10]2[S:11][C:12]([CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl>C(O)C.O.C(OCC)C>[Cl:20][C:19]1[C:7]([O:6][CH2:5][C:4]([OH:22])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH2:14][CH:15]([CH3:17])[CH3:16])[S:11][C:10]=2[C:18]=1[Cl:21]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13290078HCID 13290078, compound

Product 1

HCID 13290079HCID 13290079, compoundYield 93.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To 9.6 g of ethyl[ (6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetate in 75 ml of 95% ethanol is added 175 ml of a 6 N sodium hydroxide solution and the mixture is refluxed at 100° for 30 mins. The cooled mixture is concentrated in vacuo to give a slurry which is diluted with 500 ml of water and 500 ml of diethyl ether. With stirring and cooling, the mixture is acidified with 6 N hydrochloric acid. The acidic mixture is extracted with diethyl ether. The ether extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization of the solid from diethyl ether and hexane gives 8.3 g of [(6,7-dichloro-2-isobutylbenzo[b]thien-5-yl)oxy]acetic acid, mp 164°-165°.

Workup

  1. temperaturethe mixture is refluxed at 100° for 30 mins
  2. concentrationThe cooled mixture is concentrated in vacuo
  3. customto give a slurry which
  4. temperaturecooling
  5. extractionThe acidic mixture is extracted with diethyl ether
  6. washThe ether extracts are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent is removed
  10. customRecrystallization of the solid from diethyl ether and hexane

Sources & evidence

ORD record
ord-807f493581414b228e4142465611c85e
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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