Sodium Hydroxide → HCID 19004443, compound

HRID 2225867Notes

Reaction equation

HRID 2225867 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 86748124HCID 86748124, compound

Product 1

HCID 19004443HCID 19004443, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mix of (Z)-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 2 hours, 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 0.3 g of pure (Z)-alpha-(dimethylhydrazono)-4-[2-(2-naphthalenyloxy)ethoxy]benzeneacetic acid as a colorless solid, mp 136° C. with decomposition.

Workup

  1. temperatureheated on the steam bath for 2 hours
  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-29eec8f1082f46c5b9bfe0226bff1fe9
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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