Dimethylformamide → Methyl 2-methoxy-1-naphthoate

HRID 1604222Notes

Reaction equation

HRID 1604222 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[C:18]([OH:20])=O.CI.CN([CH:26]=[O:27])C>>[CH3:1][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]=1[C:18]([O:27][CH3:26])=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 167902-Hydroxy-1-naphthoic acid

Product 1

HCID 604022Methyl 2-methoxy-1-naphthoate

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (111 g, 803 mmol) was added to a mixture of 2-hydroxy-l-naphthoic acid (50.0 g, 266 mmol) and methyl iodide (189 g, 1330 mmol) in DMF (500 mL). The resulting mixture was heated at 80° C. overnight, then was partitioned between ether and water. The organic was washed with dilute aqueous HCl, dried (MgSO4), and concentrated to afford methyl 2-methoxynaphthoate as an oil.

Workup

  1. customwas partitioned between ether and water
  2. washThe organic was washed with dilute aqueous HCl
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e04896feb3fc42c5af3606fd74a52b8a
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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