Sodium Hydroxide → HCID 86748125, compound

HRID 2225866Notes

Reaction equation

HRID 2225866 reaction equation
C[O:2][C:3](=[O:29])/[C:4](=[N:25]/[N:26]([CH3:28])[CH3:27])/[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH3:27][N:26]([CH3:28])/[N:25]=[C:4](\[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1)/[C:3]([OH:29])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86748126HCID 86748126, compound

Product 1

HCID 86748125HCID 86748125, compoundYield 87.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (E)-alpha-(dimethylhydrazono)-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid methyl ester (0.45 g) in warm methanol (3 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (2 mL), heated on the steam bath for one hour, and the mixture was diluted with water and concentrated to remove the organic solvents. The residue was acidified with excess hydrochloric acid and extracted with dichloromethane containing a little tetrahydrofuran. The organic layer was washed with water, dried (Na2SO4), filtered and evaporated to give crude product. Crystallization from dichloromethane-hexane provided 0.38 g of pure (E)-alpha-(dimethylhydrazono)-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid as a colorless solid, mp 135° C. with decomposition.

Workup

  1. temperatureheated on the steam bath for one hour
  2. concentrationconcentrated
  3. customto remove the organic solvents
  4. extractionextracted with dichloromethane containing a little tetrahydrofuran
  5. washThe organic layer was washed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto give crude product
  10. customCrystallization from dichloromethane-hexane

Sources & evidence

ORD record
ord-4d6afea625484c1db046e47a205b9b67
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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