Toluene → 1-Naphthol

HRID 2369722Notes

Reaction equation

HRID 2369722 reaction equation
[OH2:1].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5](S(O)(=O)=O)=[CH:4][CH:3]=1.[C:13]1([CH3:19])C=CC=C[CH:14]=1>>[CH:5]1[CH:4]=[CH:3][C:2]2[C:7](=[CH:14][CH:13]=[CH:19][C:12]=2[OH:1])[CH:6]=1

Participants

3

Reactant 2

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 70051-Naphthol

Conditions

Temperature
90 °C

Procedure

The compound of the above formula (38) was dissolved in 120 ml of toluene and heated to 90° C. 57.6 g (303.0 mmol) of p-toluenesulfonic acid monohydrate was added to this solution and refluxed for 4 hours. After a reaction, the reaction product 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 (39) as 4.4 g (7.1 mmol, yield of 76%) of a white solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. customAfter a reaction
  3. washthe reaction product was washed with water
  4. customthe solvent was removed
  5. customthe obtained product was purified by column chromatography

Sources & evidence

ORD record
ord-d761bb6bf2f344acbd724349220e93c3
Source dataset
uspto-grants-2014_04
Patent number
US08709308B2

Reaction notes

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