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

HRID 913163Notes

Reaction equation

HRID 913163 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:11]([C:27]([O:29]CC)=[O:28])[C:10]=2[C:32]([O:34]CC)=[O:33])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)C>[C:1]1([CH2:7][O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[C:11]([C:27]([OH:29])=[O:28])[C:10]=2[C:32]([OH:34])=[O:33])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58012491Diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate

Product 1

HCID 4380201,4-Bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acidYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 1,4-bis[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylate (4.78 g, 9.88 mmol), ethanol (75 ml), and 2N aqueous sodium hydroxide solution (75 ml) was refluxed for 2 hours. The reaction mixture was cooled and evaporated. This was acidified with HCl (2N) and the resulting cream solid was collected by filtration and washed with water. This was dried under vacuum to give the title compound (3.79 g, 8.86 mmol). LC/MS: Rt=3.15, [MH]− 427.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated
  4. filtrationthe resulting cream solid was collected by filtration
  5. washwashed with water
  6. customThis was dried under vacuum

Sources & evidence

ORD record
ord-59c5122c778e48a6b906ff8f8f237251
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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