Methanol → Methyl 4-(hydroxymethyl)naphthalene-1-carboxylate

HRID 1166737Notes

Reaction equation

HRID 1166737 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([OH:15])=[O:14])=[CH:5][CH:4]=1.[CH3:16]O>C(OCC)(=O)C.CCCCCC>[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 111064024-Hydroxymethylnaphthoic Acid

Product 1

HCID 10878557Methyl 4-(hydroxymethyl)naphthalene-1-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-hydroxymethylnaphthoic acid (10 g, 50 mmol), methanol (300 mL), and conc. H2 SO4 (2 mL) was refluxed overnight. The insolubles were filtered off and the filtrate was concentrated. The residue was taken up in ethyl acetate and washed with aqueous NaHCO3 (2×), brine, dried over MgSO4, and concentrated to give a yellow oil. Silica gel column chromatography using ethyl acetate/hexane (1/3) gave the desired product as a yellow oil (3.3 g, 35%).

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe insolubles were filtered off
  3. concentrationthe filtrate was concentrated
  4. washwashed with aqueous NaHCO3 (2×), brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a yellow oil

Sources & evidence

ORD record
ord-34a6d02e45b1431db20ede61c2f365b4
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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