Sodium Hydroxide → HCID 19004387, compound

HRID 2225774Notes

Reaction equation

HRID 2225774 reaction equation
C[O:2][C:3](=[O:27])[C:4](=[O:26])[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]([Cl:25])[CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[Cl:25][C:7]1[CH:6]=[C:5]([C:4](=[O:26])[C:3]([OH:27])=[O:2])[CH:10]=[CH:9][C:8]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54497914HCID 54497914, compound

Product 1

HCID 19004387HCID 19004387, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-chloro-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.7 g) in warm methanol (10 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (2.5 mL) and after 10 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 0.63 g of purified 3-chloro-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 167°-168° C.

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-bc86250238684abc8af1cd3ef94fae40
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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