Methyl iodide → 1,7-Dimethoxy-2-naphthalenecarboxylic acid

HRID 35662Notes

Reaction equation

HRID 35662 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]([O:16]C)=[O:15].[C:18](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:18][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 13404481Methyl 1-hydroxy-7-methoxynaphthalene-2-carboxylate

Product 1

HCID 142567611,7-Dimethoxy-2-naphthalenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.7 g (0.016 mole) of 1-hydroxy-7-methoxy-2-naphthalenecarboxylic acid, methyl ester and 2.9 g (0.021 mole) of anhydrous potassium carbonate in 20 ml of N,N-dimethylformamide under a nitrogen atmosphere was treated with 3.0 ml (6.8 g; 0.048 mole) of iodomethane. The mixture was stirred at room temperature for 24 hours, and then added to 150 g of ice/water. The crude intermediate ester was separated by extracting with dichloromethane (3×50 ml). The combined organic layers were washed with water (2×50 ml), dried (anhydrous magnesium sulfate) and evaporated (vacuum).

Workup

  1. customThe crude intermediate ester was separated
  2. extractionby extracting with dichloromethane (3×50 ml)
  3. washThe combined organic layers were washed with water (2×50 ml)
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. customevaporated (vacuum)

Sources & evidence

ORD record
ord-e95de8aae74a4055bc51a8ae43b9b2f8
Source dataset
uspto-grants-1988_08
Patent number
US04767776

Reaction notes

Loading…