HCID 13290017, compound → HCID 13290018, compound

HRID 1903451Notes

Reaction equation

HRID 1903451 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[C:22]([Cl:23])=[C:21]([Cl:24])[C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:13]([CH3:14])[C:9]=2[CH:8]=1)C>C(O)C.[OH-].[Na+]>[Cl:23][C:22]1[C:7]([O:6][CH2:5][C:4]([OH:25])=[O:3])=[CH:8][C:9]2[C:13]([CH3:14])=[C:12]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:11][C:10]=2[C:21]=1[Cl:24]

Participants

4

Reactant 1

HCID 13290017HCID 13290017, compound

Product 1

HCID 13290018HCID 13290018, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1.5 g of ethyl[ (6,7-dichloro-3-methyl-2-phenylbenzo[b]-thien-5-yl)oxy]acetate in 50 ml of 95% ethanol and 50 ml of 15% aqueous sodium hydroxide is stirred under reflux for 1 hour. The mixture is concentrated under vacuum to dryness. The residue is triturated with water, cooled to 0° and acidified with conc hydrochloric acid. The solid product is extracted exhaustively with a mixture of ethyl ether-ethyl acetate (1:1) and the ether extracts are washed and dried over anhydrous magnesium sulfate. Removal of the solvents under reduced pressure leaves a tan-colored residue which is recrystallized from acetone to give 1.24 g of [(6,7-dichloro-3-methyl-2-phenylbenzo[b]thien-5-yl)oxy]acetic acid as shiny platelets, mp 232°-233° C.

Workup

  1. temperatureunder reflux for 1 hour
  2. concentrationThe mixture is concentrated under vacuum to dryness
  3. customThe residue is triturated with water
  4. temperaturecooled to 0°
  5. extractionThe solid product is extracted exhaustively with a mixture of ethyl ether-ethyl acetate (1:1)
  6. washthe ether extracts are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customRemoval of the solvents under reduced pressure
  9. customleaves a tan-colored residue which
  10. customis recrystallized from acetone

Sources & evidence

ORD record
ord-1855c04cfb634e24aa630da113c7afe9
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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