Sodium Hydroxide → 1,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acid

HRID 889479Notes

Reaction equation

HRID 889479 reaction equation
[CH2:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:16][CH2:17][CH3:18])=[C:7]([C:19]([O:21]CC)=[O:20])[C:6]=1[C:24]([O:26]CC)=[O:25])[CH2:2][CH3:3].[OH-].[Na+]>C(O)C.O>[CH2:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:16][CH2:17][CH3:18])=[C:7]([C:19]([OH:21])=[O:20])[C:6]=1[C:24]([OH:26])=[O:25])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58017588Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate

Product 1

HCID 210793301,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acidYield 90.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Diethyl 1,4-bis(propyloxy)-2,3-naphthalenedicarboxylate (11.45 g, 29.5 mmol) was dissolved in ethanol (70 ml) and treated with sodium hydroxide (3.54 g, 88.5 mmol) dissolved in water (15 ml). This was heated at 60° C. under argon for 4 hours. The reaction was confirmed to be complete by LC/MS and thin layer chromatography. The reaction mixture was cooled to room temperature and evaporated to a third of the volume. This was acidified to pH2 with hydrochloric acid (2N) and extracted with ethyl acetate (3×100 ml). Combined organics washed with water, brine and dried over magnesium sulphate. Solvent was evaporated to give the title compound as a yellow solid (8.91 g, 26.8 mmol).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated to a third of the volume
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washCombined organics washed with water, brine
  5. dry with materialdried over magnesium sulphate
  6. customSolvent was evaporated

Sources & evidence

ORD record
ord-5223530845704a45ae896f21604dc6ad
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

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