Hydrochloric Acid → [(2-Acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid

HRID 1903488Notes

Reaction equation

HRID 1903488 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][O:6][C:7]1[C:18]([Cl:19])=[C:17]([Cl:20])[C:10]2[S:11][C:12]([C:14](=[O:16])[CH3:15])=[CH:13][C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl.C(OCC)C>C(O)C>[C:14]([C:12]1[S:11][C:10]2[C:17]([Cl:20])=[C:18]([Cl:19])[C:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])=[CH:8][C:9]=2[CH:13]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 53636860Ethyl[(6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate

Product 1

HCID 13290041[(2-Acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acidYield 46.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5.1 g of ethyl[ (6,7-dichloro-2-acetylbenzo[b]thien-5-yl)oxy]acetate in 200 ml of 95% ethanol is added 150 ml of a 6 N sodium hydroxide solution and the mixture is refluxed at 100° for 45 mins. The solvent is removed in vacuo to give a white slurry to which is added 250 ml of a 6 N hydrochloric acid and 200 ml ethyl ether. The mixture is stirred for 2 hrs, filtered and the filter cake is distributed between 6 N hydrochloric acid and ethyl ether. The organic layers are separated and the aqueous layers are extracted with ethyl ether. The combined organic extracts are washed, dried over anhydrous magnesium sulfate, filtered and the solvent is evaporated to give a solid. Recrystallization from acetone-hexane gives 2.2 g of [(2-acetyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetic acid, mp 203°-205°.

Workup

  1. temperaturethe mixture is refluxed at 100° for 45 mins
  2. customThe solvent is removed in vacuo
  3. customto give a white slurry to which
  4. filtrationfiltered
  5. customThe organic layers are separated
  6. extractionthe aqueous layers are extracted with ethyl ether
  7. washThe combined organic extracts are washed
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent is evaporated
  11. customto give a solid
  12. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-fd5387f380c74f61ba79cef488fe036c
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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