1,4-Dihydroxy-2-naphthoic acid → HCID 4246483, compound

HRID 2166911Notes

Reaction equation

HRID 2166911 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[O-].[Na+].Cl[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl(O)(=O)=O>CO.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]([O:12][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

8

Reactant 4

HCID 6711,4-Dihydroxy-2-naphthoic acidHCID 7751Ethyl chloroacetateHCID 19654Chloric acidHCID 10942334Sodium Methoxide

Product 1

HCID 4246483HCID 4246483, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 700 ml of dimethylformamide, 249 g (1.22 mol) of 1,4-dihydroxy-2-naphthoic acid was added, and the mixture was stirred under a nitrogen atmosphere. To the mixture, 490 ml (2.44 mols) of a 28% solution of sodium methoxide in methanol was added dropwise over 20 minutes. After 10 minutes, 150 g (1.22 mol) of ethyl chloroacetate was added dropwise over 30 minutes, and the mixture was stirred for 3 hours while keeping the temperature at 50° C. The reaction solution was poured into a mixture of 160 ml of concentrated chloric acid and 5 l of iced water, and the precipitated crystals were filtered off and dried to obtain 335 g (95% yield) of 1-hydroxy-4-ethoxycarbonylmethyloxy-2-naphthoic acid.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. customat 50° C
  3. filtrationthe precipitated crystals were filtered off
  4. customdried

Sources & evidence

ORD record
ord-74519b76cc3b4089ba0b6818e62a382e
Source dataset
uspto-grants-1983_06
Patent number
US04390618

Reaction notes

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