Citric Acid → 2-Allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoic acid

HRID 1377716Notes

Reaction equation

HRID 1377716 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8])[CH:2]=[CH2:3].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[CH2:1]([O:4][C:5]1[CH:14]=[C:13]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 22914690Methyl 2-allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoate

Product 1

HCID 229146992-Allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 2-allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoate (2.50 g, 6.39 mmol) from Step 1 above in methanol (40 mL) was added 2N NaOH (15.9 mL, 31.9 mmol). The reaction mixture was refluxed for 30 minutes and cooled in a ice water bath. The solution was acidified with 5% citric acid and the solvent was evaporated under reduced pressure. The residue was dissolved in EtOAC and washed with water (2×75 mL). The organic layer was dried (MgSO4), filtered, and the solvent was evaporated under reduced pressure to give 2-allyloxy-4-(1-tertbutyloxycarbonyl-4-piperidinyloxy)benzoic acid as a white solid, which was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. temperaturecooled in a ice water bath
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAC
  5. washwashed with water (2×75 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9f8a5719f9214b2a964908052011fc7c
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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