Potassium Hydroxide → HCID 21180559, compound

HRID 1386446Notes

Reaction equation

HRID 1386446 reaction equation
[OH-].[K+].C([O:5][C:6](=[O:32])[C:7]1[C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)=[CH:11][CH:10]=[CH:9][C:8]=1[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=1)C>CO>[CH2:21]1[O:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][C:12]3[CH:11]=[CH:10][CH:9]=[C:8]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[CH:25]=4)[C:7]=3[C:6]([OH:32])=[O:5])=[CH:15][C:16]=2[O:22]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 21180554HCID 21180554, compound

Product 1

HCID 21180559HCID 21180559, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

KOH (371 mg, 5.7 mmol) that was dissolved in methanol was added to a solution of ethyl-2-(3-methoxyphenoxy)-6-[3,4-(methylenedioxy)phenoxy]benzoate (200 mg, 0.57 mmol) in methanol (5 ml). The mixture was heated under reflux for approximately 20 hours at which time TLL had indicated the formation of a polar material. The solvent was evaporated and the remaining residue was diluted with water (7 ml, pH≈7.5) and extracted with EtOAc (2×10 ml). The aqueous fraction was then acidified to pH˜2.5 using concentrated HCl and then extracted with ethyl acetate (2×10 ml). Evaporation of solvents gave an off-white solid which was recrystallized from methanol/H2O to give 146 mg (67%) of a white solid, mp 146-148° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for approximately 20 hours at which time TLL
  3. customThe solvent was evaporated
  4. additionthe remaining residue was diluted with water (7 ml, pH≈7.5)
  5. extractionextracted with EtOAc (2×10 ml)
  6. extractionextracted with ethyl acetate (2×10 ml)
  7. customEvaporation of solvents
  8. customgave an off-white solid which
  9. customwas recrystallized from methanol/H2O

Sources & evidence

ORD record
ord-c606fcb109be4a889c1c4b242ed12141
Source dataset
uspto-grants-2001_07
Patent number
US06265428B1

Reaction notes

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