Sodium Hydroxide → 1,4-Diethoxynaphthalene-2,3-dicarboxylic acid

HRID 346706Notes

Reaction equation

HRID 346706 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][CH3:16])=[C:6]([C:17]([O-:19])=[O:18])[C:5]=1[C:20]([O:22]CC)=[O:21])[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:15]([O:14][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH2:1][CH3:2])=[C:5]([C:20]([OH:22])=[O:21])[C:6]=1[C:17]([OH:19])=[O:18])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86592169Ethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate

Product 1

HCID 223445251,4-Diethoxynaphthalene-2,3-dicarboxylic acidYield 92.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl 1,4-diethoxy-2,3-naphthalenedicarboxylate (32 g, 89 mmol) was added to a solution of sodium hydroxide (20 g) in ethanol (200 ml) and water (40 ml) and stirred for 1.5 h at 60° C. The reaction was cooled and the thick white suspension was filtered. The solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml). The layers were separated and the aqueous was acidified with hydrochloric acid (2M, 120 ml). The aqueous was extracted with ethyl acetate (2×) and the combined organics were dried (MgSO4). Evaporation of the solvent under vacuum gave the title compound as a white solid (25 g, 92%).

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe thick white suspension was filtered
  3. dissolutionThe solid was dissolved in a mixture of ethyl acetate (200 ml) and water (800 ml)
  4. customThe layers were separated
  5. extractionThe aqueous was extracted with ethyl acetate (2×)
  6. dry with materialthe combined organics were dried (MgSO4)
  7. customEvaporation of the solvent under vacuum

Sources & evidence

ORD record
ord-264f6188805e4e2e9d8f578989608fcc
Source dataset
uspto-grants-2007_02
Patent number
US07173047B2

Reaction notes

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