Dimethylformamide → Methyl 2-methoxy-1-naphthoate

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Methyl iodide	HCID 6328	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Hydroxy-1-naphthoic acid	HCID 16790	—
Product	Methyl 2-methoxy-1-naphthoate	HCID 604022	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05994270
Source dataset	uspto-grants-1999_11
ORD ID	ord-e04896feb3fc42c5af3606fd74a52b8a
Source note	uspto-grants-1999_11