Sodium Hydroxide → HCID 13290186, compound

HRID 652648Notes

Reaction equation

HRID 652648 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 hydrocloric 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-e32c23b3fe4645498f5d504d9079903a
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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