1,4-Dihydroxy-2-naphthoic acid → Methyl 1,4-dihydroxy-2-naphthoate

HRID 2369627Notes

Reaction equation

HRID 2369627 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].[C:16]([O-])(O)=O.[Na+].CI.O>CN(C)C=O>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 6711,4-Dihydroxy-2-naphthoic acidHCID 962WaterHCID 6328Methyl iodideHCID 516892Sodium Bicarbonate

Product 1

HCID 604167Methyl 1,4-dihydroxy-2-naphthoateYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Dihydroxy-2-naphthoic acid (10 g, 49 mmol) and NaHCO3 (4.12 g, 49 mmol) was dissolved in DMF (dimethylformamide) (50 mL). Methyl iodide (6.96 g, 49 mmol) was added and the solution stirred at room temperature for 24 h, poured into water (1 L), filtered and washed with water to give the title compound (8.80 g, 82%) as a green powder.

Workup

  1. filtrationfiltered
  2. washwashed with water

Sources & evidence

ORD record
ord-85f82f36358b4ecb9d2d94ba7a6cc5e8
Source dataset
uspto-grants-2014_04
Patent number
US08703978B2

Reaction notes

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