Sodium Hydroxide → HCID 13290186, compound

HRID 1903472Notes

Reaction equation

HRID 1903472 reaction equation
C([O:3][C:4](=[O:24])[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])=[CH:13][S:12][C:11]=2[C:22]=1[Cl:23])C.[OH-].[Na+]>C(O)C>[Cl:23][C:22]1[C:11]2[S:12][CH:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[F:21])[C:10]=2[CH:9]=[CH:8][C:7]=1[O:6][CH2:5][C:4]([OH:24])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13985633HCID 13985633, compound

Product 1

HCID 13290186HCID 13290186, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.2 g of ethyl{ [7-chloro-3-(2-fluorophenyl)benzo[b]thien-6-yl]oxy}acetate, 150 ml of 20% sodium hydroxide solution and 150 ml of 95% ethanol is stirred under reflux for 90 minutes. The reaction mixture is evaporated under reduced pressure, 200 ml of water is added and the solution is acidified with concentrated hydrochloric acid. The mixture is extracted with four 200 ml portions of ether. The combined organic extracts are dried over anhydrous magnesium sulfate, filtered and concentrated to give a crystalline material. Recrystallization from acetone-hexane provides {[7-chloro-3-(2-fluorophenyl)benzo[b]thien-6-yl]oxy}acetic acid as needles, mp 163°-164° C.

Workup

  1. temperatureunder reflux for 90 minutes
  2. customThe reaction mixture is evaporated under reduced pressure, 200 ml of water
  3. additionis added
  4. extractionThe mixture is extracted with four 200 ml portions of ether
  5. dry with materialThe combined organic extracts are dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crystalline material
  9. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-df12155f3abf43629b4287d0cb77aacd
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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