Sodium Hydroxide → 1-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid

HRID 222431Notes

Reaction equation

HRID 222431 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][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([C:22]([O:24]CC)=[O:23])[C:5]=1[C:27]([O:29]CC)=[O:28])[CH3:2].[OH-].[Na+]>C(O)C>[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][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([C:22]([OH:24])=[O:23])[C:5]=1[C:27]([OH:29])=[O:28])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58012512Diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

Product 1

HCID 580124801-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate (3.05 g, 7.23 mmol), ethanol (30 ml), and 2N aqueous sodium hydroxide solution (35 ml) was refluxed for 3 hours. The reaction mixture was cooled and evaporated. This was acidified with HCl (2N) and extracted with ethyl acetate twice. Combined organics were dried over magnesium sulphate and the solvent evaporated to give the title compound as a white solid (2.55 g, 6.97 mmol). LC/MS: Rt=2.76, [MH]− 365.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. extractionextracted with ethyl acetate twice
  5. dry with materialCombined organics were dried over magnesium sulphate
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-d162371733ad4c0cb011c193a73568c8
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

Loading…