Cyclohexanecarboxaldehyde → HCID 66771669, compound

HRID 1025267Notes

Reaction equation

HRID 1025267 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([OH:11])[CH:5]=1.[CH:13]1([CH:19]=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C>CO>[CH:13]1([C:19]2[O:11][C:6]3[CH:5]=[C:4]([C:3]([OH:2])=[O:12])[CH:9]=[CH:8][C:7]=3[N:10]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 16275CyclohexanecarboxaldehydeHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterHCID 178418268HCID 178418268, compound

Product 1

HCID 66771669HCID 66771669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino-3-hydroxy-benzoic acid methyl ester (5 g, 29.91 mmol) in CH3OH (150 mL) was added cyclohexanecarbaldehyde (3.6 mL, 29.91 mmol) at room temperature. The resulting mixture was stirred at room temperature for 2 h. The solvent was removed by evaporation and CH3CN (150 mL) was added to the residue. Lead (IV) acetate (13.26 g, 29.91 mmol) was added as one portion under N2 and the resulting mixture was refluxed for 10 min. After cooling, the resulting solid was filtered and washed with CH3CN. To the filtrate was then added 3N NaOH (40 mL). The resulting mixture was stirred at 50° C. for 18 h. The solvent was removed by evaporation and the resulting residue was purified by flash chromatography on silica gel to yield 2-cyclohexyl-benzooxazole-6-carboxylic acid. MS m/z (M+H+) 246.2.

Workup

  1. customThe solvent was removed by evaporation and CH3CN (150 mL)
  2. additionwas added to the residue
  3. temperaturethe resulting mixture was refluxed for 10 min
  4. temperatureAfter cooling
  5. filtrationthe resulting solid was filtered
  6. washwashed with CH3CN
  7. additionTo the filtrate was then added 3N NaOH (40 mL)
  8. stirringThe resulting mixture was stirred at 50° C. for 18 h
  9. customThe solvent was removed by evaporation
  10. customthe resulting residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e35bfa57eafa4098bb773eb5be7c3a3f
Source dataset
uspto-grants-2014_05
Patent number
US08729064B2

Reaction notes

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