Methanol → HCID 10036901, compound

HRID 502620Notes

Reaction equation

HRID 502620 reaction equation
[OH:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.S(=O)(=O)(O)O.[CH3:22]O>C(OCC)C>[CH3:22][O:15][C:14]([C:3]1[C:2]([OH:1])=[CH:11][C:10]2[C:5](=[CH:6][C:7]([O:12][CH3:13])=[CH:8][CH:9]=2)[CH:4]=1)=[O:16]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6083303-Hydroxy-7-methoxy-2-naphthoic acid

Product 1

HCID 10036901HCID 10036901, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid (2.5 g, 11.45 mmol) in 50 mL methanol was added 0.3 mL of concentrated sulfuric acid. The resulting mixture was heated at reflux for 18 hours, then cooled and diluted with diethyl ether. The organic phase was washed with water and saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered and concentrated under reduced pressure to give 2.51 g of 3-hydroxy-7-methoxy-naphthalene-2-carboxylic acid methyl ester, MP=129-131° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperaturecooled
  4. washThe organic phase was washed with water and saturated aqueous sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b66b6ebd5fc42ffb59fff4e0435f4a8
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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