Water → HCID 68527500, compound

HRID 237766Notes

Reaction equation

HRID 237766 reaction equation
O[C:2]1([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[C:2]1([C:8]2[N:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 68524570HCID 68524570, compound

Product 1

HCID 68527500HCID 68527500, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 6-(1-hydroxy-cyclohexyl)-pyridin-3-ol (2.5 g, 12.9 mmol) in toluene (130 mL) was added p-toluenesulfonic acid monohydrate (8.12 g, 42.7 mmol). The mixture was refluxed with azeotropic removal of water for 2 hours. The reaction mixture was cooled to room temperature, neutralized with aqueous NaHCO3 and extracted three times with EtOAc. The organic phase was washed with brine, dried (Na2SO4), passed through a silica gel pad and concentrated to provide the title compound as a solid (2.2 g).

Workup

  1. extractionextracted three times with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b0ecb34658784caea30c2fbf5e0ba749
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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