Hydrochloric Acid → 4-Methyl-1-naphthol

HRID 619872

Reaction equation

HRID 619872 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12]C)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.Cl>>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 43814674-Methoxy-1-methylnaphthaleneHCID 10176127Pyridinium chloride

Product 1

HCID 824834-Methyl-1-naphthol

Conditions

Temperature
200 °C

Procedure

4-Methyl-1-methoxynaphthalene (4) (145 g) was mixed with pyridine hydrochloride (250 g) and the mixture was heated at 200° C. for 3 hours. The mixture was cooled, treated with dilute hydrochloric acid, and extracted with ether. The ether extract was dried (MgSO4), filtered and the solvent removed, leaving a black oil which was extracted with petroleum b.p. 60°-80° C. (4×100 cm3). 4-Methyl-1-naphthol (5) was obtained as near colourless oily crystals which darken on storage.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed
  7. customleaving a black oil which
  8. extractionwas extracted with petroleum b.p. 60°-80° C. (4×100 cm3)

Sources & evidence

ORD record
ord-f30e9ede785445388d3e53904cba5691
Source dataset
uspto-grants-1989_04
Patent number
US04818096

Linked notes

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