Hydrochloric Acid → HCID 22761128, compound

HRID 1704089Notes

Reaction equation

HRID 1704089 reaction equation
C[O:2][C:3](=[O:32])[CH:4]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:23]=1)[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)=[CH:7][CH:6]=1.[OH-].[K+].Cl>C(O)C.O>[C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[O:21][CH:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[CH:7][CH:6]=1)[C:3]([OH:32])=[O:2])([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 131711325HCID 131711325, compound

Product 1

HCID 22761128HCID 22761128, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 9.5 g of methyl(m-tert.-butylphenoxy){p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 60 ml of ethanol is added a solution of 7 g of potassium hydroxide in 60 ml of water. The mixture is stirred and refluxed for 18 hours and while hot is acidified with 11.5 ml of concentrated HCl. The mixture is chilled immediately. The supernatant is decanted from the oil which separates. Water is added and decanted. The gummy material is dissolved in dichloromethane, dried (MgSO4) and the solvent removed under reduced pressure to give 8.4 g of a gum. The gum is triturated with hexane containing a small amount of dichloromethane to give 5.7 g of yellow crystals. The crystals are dissolved in 25 ml of dichloromethane and the solution diluted with 50 ml of hexane. Chilling gives 4.4 g of product as pale yellow crystals, mp 122°-124° C.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureThe mixture is chilled immediately
  3. customThe supernatant is decanted from the oil which
  4. additionWater is added
  5. customdecanted
  6. dissolutionThe gummy material is dissolved in dichloromethane
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-fe6fedd9aafc463a8533abf7e5b1d9ae
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

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