Hydrochloric Acid → HCID 22761162, compound

HRID 1704109Notes

Reaction equation

HRID 1704109 reaction equation
C[C:2]([O:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:27][CH:26]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[OH-].[K+].O.Cl>C(O)C>[CH2:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][CH:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])=[CH:26][CH:27]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 22761153HCID 22761153, compound

Product 1

HCID 22761162HCID 22761162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.5 g of methyl(p-benzyloxyphenoxy){p-[3-(p-chlorophenoxy)propoxy]phenyl}acetic acid, 5.5 g of potassium hydroxide, 3 ml of water and 150 ml of ethanol is refluxed for 4 hours. The mixture is acidified with concentrated HCl and extracted with chloroform. The extract is dried (MgSO4) and the solvent removed under reduced pressure. The oil is dissolved in benzene and the solution diluted with hexane. On standing, crystals separate and are filtered off and recrystallized from benzene-hexane to give 2.15 g of light tan crystals, mp 105°-109° C.

Workup

  1. temperatureis refluxed for 4 hours
  2. extractionextracted with chloroform
  3. dry with materialThe extract is dried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe oil is dissolved in benzene
  6. additionthe solution diluted with hexane
  7. customcrystals separate
  8. filtrationare filtered off
  9. customrecrystallized from benzene-hexane
  10. customto give 2.15 g of light tan crystals, mp 105°-109° C.

Sources & evidence

ORD record
ord-1e3141a99051425f9702058f1bf75952
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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