Methanol → Methyl 4-hydroxynaphthalene-1-carboxylate

HRID 1823111Notes

Reaction equation

HRID 1823111 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:20]O>O.C(OCC)(=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:20])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3442911-Hydroxy-4-naphthoic acid

Product 1

HCID 22171384Methyl 4-hydroxynaphthalene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxy-1-naphthoic acid (2.18 g) in methanol (15 ml) was added sulfuric acid (1.0 ml), and the mixture was stirred at 70° C. for 3 hours. The solution was diluted with water and ethyl acetate. The organic layer was separated and washed with brine. The extract was dried over magnesium sulfate, filtrated and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with ethyl acetate and hexane to give methyl 4-hydroxy-1-naphthoate (1.64 g) as a white solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialThe extract was dried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel with ethyl acetate and hexane

Sources & evidence

ORD record
ord-e46ac103bc1e4fdba937d43c639e1cdd
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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