Oxalyl chloride → Methyl 3-hydroxynaphthalene-1-carboxylate

HRID 2185885

Reaction equation

HRID 2185885 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:15](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 1902323-Hydroxy-1-naphthoic acid

Product 1

HCID 23423090Methyl 3-hydroxynaphthalene-1-carboxylateYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-hydroxy-1-naphthalenecarboxylic acid (6.67 g, 35.4 mmol) and oxalyl chloride (3.86 mL, 44.2 mmol) in DCM (150 mL) was added 3 drops of DMF. The mixture was stirred at room temperature for 3 h., the solvent was removed under reduced pressure and methanol (150 mL) was added. After stirring at reflux for 15 min the solvent was removed under reduced pressure, the residue was purified by column chromatography (10%, 20% and 30% EtOAc/hexane) to give the title compound as a yellow solid (2.5 g, 35%). 1H NMR (DMSO-d6) δ 10.10 (s, 1H), 8.61 (d, 1H), 7.77 (d, 1H), 7.72 (d, 1H), 7.47 (m, 2H), 7.38 (d, 1H), 3.93 (s, 3H); MS m/z 201.1 (M−H).

Workup

  1. customthe solvent was removed under reduced pressure and methanol (150 mL)
  2. additionwas added
  3. stirringAfter stirring
  4. temperatureat reflux for 15 min the solvent
  5. customwas removed under reduced pressure
  6. customthe residue was purified by column chromatography (10%, 20% and 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-6f31a575f07b468da6155b9f28e6b5a0
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Linked notes

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