p-Toluenesulfonic acid → 1-Naphthol

HRID 1875286Notes

Reaction equation

HRID 1875286 reaction equation
[C:1]12(CS(O)(=O)=O)[C:8]([CH3:10])(C)[CH:5]([CH2:6][CH2:7]1)[CH2:4][C:2]2=[O:3].[C:16]1(C)C=CC(S(O)(=O)=O)=C[CH:17]=1>C1(C)C=CC=CC=1>[CH:16]1[CH:10]=[CH:8][C:1]2[C:7](=[CH:6][CH:5]=[CH:4][C:2]=2[OH:3])[CH:17]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-

Product 1

HCID 70051-Naphthol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The compound of the above formula (30) and 221.1 mg (0.9 mmol) of (±)-10-camphorsulfonic acid were dissolved in 150 ml of toluene and refluxed for 30 minutes. The resulting solution was left to be cooled to room temperature, added to 100 ml of a toluene solution of 4.5 g (27.3 mmol) of p-toluenesulfonic acid heated at 90° C. and refluxed for 4 hours. After the reaction, the reaction solution was washed in water, the solvent was removed, and the obtained product was purified by column chromatography to obtain a naphthol compound represented by the following formula (31) as 3.7 g (8.2 mmol, yield rate of 45%) of a yellow solid.

Workup

  1. temperaturerefluxed for 30 minutes
  2. waitThe resulting solution was left
  3. temperatureheated at 90° C.
  4. temperaturerefluxed for 4 hours
  5. customAfter the reaction
  6. washthe reaction solution was washed in water
  7. customthe solvent was removed
  8. customthe obtained product was purified by column chromatography

Sources & evidence

ORD record
ord-96c10e29e8b240298aafa772dad54325
Source dataset
uspto-grants-2012_11
Patent number
US08308996B2

Reaction notes

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