Sodium Hydroxide → HCID 57557633, compound

HRID 2237768Notes

Reaction equation

HRID 2237768 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([O:15][CH2:16][CH3:17])=[C:6]([C:18]([O:20]CC)=[O:19])[C:5]=1[C:23]([O:25]CC)=[O:24])[CH3:2].[OH-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([O:15][CH2:16][CH3:17])=[C:6]([C:18]([OH:20])=[O:19])[C:5]=1[C:23]([OH:25])=[O:24])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57557634HCID 57557634, compound

Product 1

HCID 57557633HCID 57557633, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 1,4-bis(ethyloxy)-6-fluoro-2,3-naphthalenedicarboxylate (2.5 g, 6.6 mmol), ethanol (50 ml) and sodium hydroxide (50 ml) was heated under reflux for 1 hour. The reaction mixture was cooled and concentrated in vacuo. This was acidified with 2N HCl (˜50 ml) and extracted with EtOAc (×2). Combined organics were washed with brine, dried over magnesium sulphate and concentrated in vacuo to give the title compound as a yellow solid (2.24 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. extractionextracted with EtOAc (×2)
  6. washCombined organics were washed with brine
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e74843bd0ee4e56ac21f7d00f184edf
Source dataset
uspto-grants-2010_05
Patent number
US07718689B2

Reaction notes

Loading…