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

HRID 889480Notes

Reaction equation

HRID 889480 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]CC)=[O:18])[C:5]=1[C:22]([O:24]CC)=[O:23])[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:22]([OH:24])=[O:23])[C:6]=1[C:17]([OH:19])=[O:18])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21393755Diethyl 1,4-diethoxynaphthalene-2,3-dicarboxylate

Product 1

HCID 223445251,4-Diethoxynaphthalene-2,3-dicarboxylic acidYield 89.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Diethyl 1,4-bis(ethyloxy)-2,3-naphthalenedicarboxylate (24.8 g, 68.8 mmol) was suspended in ethanol (200 ml) and treated with sodium hydroxide (8.3 g, 206.4 mmol) dissolved in 200 ml of water. A further 50 ml of ethanol added to aid stirring. Heated to reflux, 100° C. All in solution on heating. Refluxed for 8 hours. Cooled to room temperature and stood overnight. Solvent was evaporated to almost dryness. Water was added and stirred in an ice bath. Acidified with 2M HCl solution (˜150 ml). The white precipitate was filtered, washed with water and dried in a vacuum oven to give the title compound as a white solid (18.77 g, 61.7 mmol).

Workup

  1. temperatureHeated
  2. temperatureAll in solution on heating
  3. temperatureRefluxed for 8 hours
  4. temperatureCooled to room temperature
  5. customSolvent was evaporated to almost dryness
  6. additionWater was added
  7. stirringstirred in an ice bath
  8. filtrationThe white precipitate was filtered
  9. washwashed with water
  10. customdried in a vacuum oven

Sources & evidence

ORD record
ord-0d9cba439914478cbfe742c6de44b858
Source dataset
uspto-grants-2012_08
Patent number
US08252833B2

Reaction notes

Loading…