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

HRID 913173Notes

Reaction equation

HRID 913173 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 2× ethyl acetate. 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 2× ethyl acetate
  5. dry with materialCombined organics were dried over magnesium sulphate
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-f1cbce3a73e64497b7e726dbffbfee56
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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