HCID 13290023, compound → HCID 13290024, compound

HRID 370959Notes

Reaction equation

HRID 370959 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[C:16]([Cl:17])=[C:15]([Cl:18])[C:10]2[S:11][C:12]([CH3:14])=[CH:13][C:9]=2[CH:8]=1)C>[OH-].[Na+].C(O)C>[Cl:17][C:16]1[C:7]([O:6][CH2:5][C:4]([OH:19])=[O:3])=[CH:8][C:9]2[CH:13]=[C:12]([CH3:14])[S:11][C:10]=2[C:15]=1[Cl:18]

Participants

4

Reactant 1

HCID 13290023HCID 13290023, compound

Product 1

HCID 13290024HCID 13290024, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2.6 g of ethyl[(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetate in 20 ml of 20% sodium hydroxide solution and 20 ml of ethanol is warmed on a steam bath for 1 hour. The cooled mixture is concentrated in vacuo to remove the ethanol and the aqueous mixture is acidified with conc. hydrochloric acid to pH 2. After stirring at room temperature for 2 hours, the solid collected on a filter, dried and recrystallized from acetone-hexane to give 2.0 g of [(6,7-dichloro-2-methylbenzo[b]thien-5-yl)oxy]acetic acid as white needles, mp 215°-216°.

Workup

  1. temperatureis warmed on a steam bath for 1 hour
  2. concentrationThe cooled mixture is concentrated in vacuo
  3. customto remove the ethanol
  4. customthe solid collected on a filter
  5. customdried
  6. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-0097ce6cf855473b9381def382555957
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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