p-Toluenesulfonic acid → 1-Naphthol

HRID 2369724Notes

Reaction equation

HRID 2369724 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 (48) and 221.1 mg (0.9 mmol) of (±)-10-camphorsulfonic acid were dissolved in 150 ml of toluene and refluxed for 30 minutes. After the obtained solution was left to be cooled to room temperature, this solution was added to 100 ml of a toluene solution containing 4.5 g (27.3 mmol) of p-toluenesulfonic acid heated at 90° C. and refluxed for 4 hours. After a reaction, the reaction solution was washed with water, the solvent was removed, and the obtained product was purified by column chromatography to obtain a naphthol compound represented by the following formula (49) as 3.7 g (8.2 mmol, yield of 45%) of a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-fbbe37de6fea4f399304c6e61b2048da
Source dataset
uspto-grants-2014_04
Patent number
US08709308B2

Reaction notes

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