Hydrochloric Acid → 3-Methoxynaphthalen-1-ol

HRID 434022Notes

Reaction equation

HRID 434022 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([OH:12])[CH:3]=1.Cl.[CH3:14]O>>[CH3:14][O:12][C:4]1[CH:3]=[C:2]([OH:1])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86011,3-Dihydroxynaphthalene

Product 1

HCID 109975333-Methoxynaphthalen-1-olYield 57%

Procedure

To a stirring solution of 1,3-dihydroxynaphthalene (2.31 g, 14.4 mmol) in methanol (150 mL) at 0° C., hydrochloride gas was bubbed for 10 min. The resulting solution was continued stirring at room temperature for 24 hrs. A residue was obtained after evaporation of methanol and purified by silica gel column chromatography eluted with chloroform to provide the title compound as purple crystals (1.42 g, 57%). 1H NMR(300 MHz CDCl3) δ8.08(d, 1H), 7.70(d, 1H), 7.46(t, 1H), 7.34(t, 1H), 6.78 (s, 1H), 6.54 (s, 1H), 5.61(s, 1H), 3.90(s, 3H).

Workup

  1. customA residue was obtained
  2. customafter evaporation of methanol
  3. custompurified by silica gel column chromatography
  4. washeluted with chloroform

Sources & evidence

ORD record
ord-8d938b766bc24309b877d645d4084309
Source dataset
uspto-grants-2003_12
Patent number
US06670387B1

Reaction notes

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