Hexane → HCID 20559487, compound

HRID 1659557Notes

Reaction equation

HRID 1659557 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][CH:19]([CH3:25])[C:20]([O:22]CC)=[O:21])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.CCCCCC>CO>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][O:18][CH:19]([CH3:25])[C:20]([OH:22])=[O:21])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 14797Potassium HydroxideHCID 20559484HCID 20559484, compound

Product 1

HCID 20559487HCID 20559487, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (5.5 g.) was added to a solution of ethyl 2-{2-[4-(4-chlorophenyl)phenyl]-ethoxy}propionate (7.0 g.) in methanol (50 ml.), and the resultant solution was heated under reflux for 2 hours. The mixture was cooled and solvent removed by evaporation, the residue was mixed with water (50 ml.) and the solution obtained was extracted with ether (2×50 ml.) to remove non-acidic material. The aqueous phase was acidified with 4 N-hydrochloric acid to pH 2-3 and extracted with ethyl acetate (3×50 ml.). The extracts were washed with water, dried (MgSO4) and evaporated. The oil obtained, solidified on trituration with hexane to give 2-{2-[4-(4-chlorophenyl)phenyl]-ethoxy}propionic acid (3.9 g., 57%), m.p. 90°-92° C. (after recrystallisation from a mixture of hexane and toluene), molecular ion: M+ 304.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureThe mixture was cooled
  3. customsolvent removed by evaporation
  4. additionthe residue was mixed with water (50 ml.)
  5. customthe solution obtained
  6. extractionwas extracted with ether (2×50 ml.)
  7. customto remove non-acidic material
  8. extractionextracted with ethyl acetate (3×50 ml.)
  9. washThe extracts were washed with water
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe oil obtained

Sources & evidence

ORD record
ord-4c1881c439e4413da1c5cddb2caded7f
Source dataset
uspto-grants-1981_12
Patent number
US04304788

Reaction notes

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