Sodium Hydroxide → HCID 20559495, compound

HRID 1659560Notes

Reaction equation

HRID 1659560 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:16][CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([O:16][CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH3:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20559492HCID 20559492, compound

Product 1

HCID 20559495HCID 20559495, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-{1-[4-(4-chlorophenyl)-phenyl]-ethoxy}propionate (3.0 g.) in a mixture of ethanol (150 ml.) and water (5 ml.), containing sodium hydroxide (5.0 g.), was heated under reflux for 5 hours. The mixture was then evaporated and the residue diluted with water (50 ml.) and extracted with ether. The ether extract was discarded and the aqueous alkaline phase was acidified to pH 1-3 by addition of concentrated hydrochloric acid. The mixture was extracted thoroughly with ether. The combined extracts were washed with water, dried (MgSO4), and evaporated. The residue was triturated with petrol (40-60) and the solid which formed was separated and recrystallised from toluene to give 2-{1-[4-(4-chlorophenyl)phenyl]ethoxy}propionic acid, m.p. 144°-146° C. in 26% yield.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe mixture was then evaporated
  4. additionthe residue diluted with water (50 ml.)
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. additionthe aqueous alkaline phase was acidified to pH 1-3 by addition of concentrated hydrochloric acid
  8. extractionThe mixture was extracted thoroughly with ether
  9. washThe combined extracts were washed with water
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe residue was triturated with petrol (40-60)
  13. customthe solid which formed
  14. customwas separated
  15. customrecrystallised from toluene

Sources & evidence

ORD record
ord-6486c4a49a6b4c939758aa48c1582995
Source dataset
uspto-grants-1981_12
Patent number
US04304788

Reaction notes

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