Sodium Hydroxide → HCID 19004422, compound

HRID 2225770Notes

Reaction equation

HRID 2225770 reaction equation
C[O:2][C:3](=[O:29])[C:4](=[O:28])[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)=[C:7]([N+:25]([O-:27])=[O:26])[CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[O:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:28])[C:3]([OH:29])=[O:2])=[CH:6][C:7]=1[N+:25]([O-:27])=[O:26]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54416410HCID 54416410, compound

Product 1

HCID 19004422HCID 19004422, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[2-(2-naphthalenyloxy)ethoxy]-3-nitro-alpha-oxobenzeneacetic acid methyl ester (0.55 g) in warm methanol (10 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (2 mL) and after 5 minutes 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 acetone-hexane provided 0.42 g of purified 4-[2-(2-naphthalenyloxy)ethoxy]-3-nitro-alpha-oxobenzeneacetic acid as a yellow solid, mp 164° C. with decomposition.

Workup

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

Sources & evidence

ORD record
ord-642245c0cc9b4733b9371520568cafbf
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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