Methanol → Methyl 6-methoxy-2-naphthoate

HRID 1695218Notes

Reaction equation

HRID 1695218 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2.S(=O)(=O)(O)O.[CH3:21]O>>[CH3:21][O:14][C:13]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 3491816-Methoxy-2-Naphthoic Acid

Product 1

HCID 604020Methyl 6-methoxy-2-naphthoateYield 94%

Conditions

Temperature
80 °C

Procedure

To a solution of 6-methoxy-naphthalene-2-carboxylic acid (1.01 g, 5 mmol) in methanol (10 mL), a catalytic amount of sulphuric acid was added. The mixture was then heated at 80° C. for 8 hours. Upon reaction completion (as monitored by LcMS), the solution was slowly cooled and the precipitation of the product was observed. Filtration of the white solid afforded 1.01 g (94% yield) of title compound

Workup

  1. customUpon reaction completion (as monitored by LcMS)
  2. temperaturethe solution was slowly cooled
  3. customthe precipitation of the product
  4. filtrationFiltration of the white solid

Sources & evidence

ORD record
ord-61f79c62b579444a952a978a3bde4ea4
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

Loading…