Dimethylformamide → Methyl 3-Methoxy-2-naphthoate

HRID 1388673Notes

Reaction equation

HRID 1388673 reaction equation
[OH:1][C:2]1[C:3]([C:12]([OH:14])=O)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.CI.[C:17](=O)([O-])[O-].[K+].[K+].CN(C)[CH:25]=[O:26]>O>[CH3:17][O:1][C:2]1[C:3]([C:12]([O:26][CH3:25])=[O:14])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 71043-Hydroxy-2-naphthoic acidHCID 11430Potassium Carbonate

Product 1

HCID 296952Methyl 3-Methoxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 18.8 g. (0.1 mole) of 3-hydroxy-2-naphthoic acid, 20 ml. of methyl iodide, 28 g. of potassium carbonate, and 200 ml. of N,N-dimethylformamide was heated at 70° C. for 16 hours, then poured into 1 liter of water. The mixture was extracted with diethyl ether and the extracts were washed with water, then 5 percent sodium hydroxide solution, then water again, and dried over magnesium sulfate. Evaporation provided a residue of methyl 3-methoxy-2-naphthoate.

Workup

  1. additionA mixture of 18.8 g
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe extracts were washed with water
  4. dry with material5 percent sodium hydroxide solution, then water again, and dried over magnesium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-2660ec040ce8472c964963172aa358d4
Source dataset
uspto-grants-1984_02
Patent number
US04432986

Reaction notes

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