Sodium Hydroxide → HCID 19004512, compound

HRID 2225787Notes

Reaction equation

HRID 2225787 reaction equation
C[O:2][C:3](=[O:30])[C:4](=[O:29])[C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([O:13][CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[C:7]([F:27])[C:6]=1[F:28].[OH-].[Na+]>CO.O1CCCC1.O>[F:11][C:10]1[C:9]([F:12])=[C:8]([O:13][CH2:14][CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[C:7]([F:27])=[C:6]([F:28])[C:5]=1[C:4](=[O:29])[C:3]([OH:30])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 54150432HCID 54150432, compound

Product 1

HCID 19004512HCID 19004512, compoundYield 38.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3,5,6-tetrafluoro-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in warm methanol (10 mL) and tetrahydrofuran (10 mL) was treated with 1N sodium hydroxide (2 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 dichloromethane-hexane provided 0.185 g of purified 2,3,5,6-tetrafluoro-4-[2-(2-naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid as a yellow solid, mp 146°-148° 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 dichloromethane-hexane

Sources & evidence

ORD record
ord-28d474a8a7174da6b73ff955d2ea10e4
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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