Hydrochloric Acid → HCID 22761157, compound

HRID 1704087Notes

Reaction equation

HRID 1704087 reaction equation
C[C:2]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[OH-].[K+].Cl>C(O)C.O>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:25]=[CH:24][C:23]([O:22][CH:2]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[CH:8][CH:7]=2)[C:3]([OH:5])=[O:4])=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22761152HCID 22761152, compound

Product 1

HCID 22761157HCID 22761157, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 8.5 g of methyl(α,α,α-trifluoro-p-tolyloxy){p-[(p-chlorophenoxy)methoxy]phenyl}acetic acid in 50 ml of ethanol is added a solution of 6 g of potassium hydroxide in 50 ml of water. The mixture is refluxed for 4 hours and while hot, is acidified with 10 ml of concentrated HCl. The mixture is chilled immediately and extracted with dichloromethane. The extract is washed with a solution of sodium chloride, dried (MgSO4) and the solvent is removed under reduced pressure. The residue is triturated with hexane containing small amounts of ether and dichloromethane and chilled to give 6.7 g of product as white crystals. The product is recrystallized by dissolving in 50 ml of benzene, filtering the solution and diluting the filtrate with 75 ml of hexane. Chilling and filtering gives 6.1 g of white crystals, mp 88°-89° C.

Workup

  1. temperatureThe mixture is refluxed for 4 hours
  2. temperatureThe mixture is chilled immediately
  3. extractionextracted with dichloromethane
  4. washThe extract is washed with a solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is triturated with hexane containing small amounts of ether and dichloromethane
  8. temperaturechilled

Sources & evidence

ORD record
ord-766c0e6fadd84309ba304d4a28060d47
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

Loading…