Hydrochloric Acid → HCID 13290065, compound

HRID 371001Notes

Reaction equation

HRID 371001 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[C:17]([Cl:18])=[C:16]([Cl:19])[C:10]2[S:11][C:12]([CH3:15])=[C:13]([CH3:14])[C:9]=2[CH:8]=1)C.[OH-].[Na+].Cl>C(O)C>[Cl:18][C:17]1[C:7]([O:6][CH2:5][C:4]([OH:20])=[O:3])=[CH:8][C:9]2[C:13]([CH3:14])=[C:12]([CH3:15])[S:11][C:10]=2[C:16]=1[Cl:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13290064HCID 13290064, compound

Product 1

HCID 13290065HCID 13290065, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 22.0 g of ethyl[(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetate and 600 ml of 95% ethanol is added 600 ml of 20% sodium hydroxide solution and the mixture is refluxed for 2 hrs. Most of the solvent is removed in vacuo to give a white slurry to which is added 600 ml of a 6N hydrochloric acid. After stirring for about 3 hrs, the mixture is filtered. The solid is taken up in 1:1-ethyl acetate-ethyl ether. The organic layers are washed, dried and filtered and the solvent is removed to give a solid. Recrystallization from acetone-hexane gives 17.1 g of [(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetic acid, mp 218°-219°.

Workup

  1. temperaturethe mixture is refluxed for 2 hrs
  2. customMost of the solvent is removed in vacuo
  3. customto give a white slurry to which
  4. filtrationthe mixture is filtered
  5. washThe organic layers are washed
  6. customdried
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customto give a solid
  10. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-781a639c9a2d4709b6e3d27349b87eb8
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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