Sodium Hydroxide → HCID 19004331, compound

HRID 2225718Notes

Reaction equation

HRID 2225718 reaction equation
C[O:2][C:3](=[O:36])[C:4](=[O:35])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:24]([O:25][CH2:26][CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[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>[O:35]=[C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:24]([O:25][CH2:26][CH2:27][O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[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:36])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67757190HCID 67757190, compound

Product 1

HCID 19004331HCID 19004331, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of alpha-oxo-4-[[2-[3-(2-phenoxyethoxy)-2-naphthalenyloxy]ethyl]oxy]benzeneacetic acid methyl ester (0.50 g) in hot methanol (10 mL) plus enough tetrahydrofuran to dissolve the solids, was treated with 1N sodium hydroxide (2 mL) and diluted with water. The organic solvent was removed under vacuum and the residue was mixed with water, acidified with excess 2N hydrochloric acid, and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from acetone-hexane provided 0.45 g of alpha-oxo-4-[[2-[3-(2-phenoxyethoxy)-2-naphthalenyloxy]ethyl]oxy]benzeneacetic acid as a colorless solid, mp 176°-177° C.

Workup

  1. dissolutionto dissolve the solids
  2. customThe organic solvent was removed under vacuum
  3. additionthe residue was mixed with water
  4. extractionextracted with dichloromethane
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product
  9. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-0f7a614f09c5400eba99644c8d0a867b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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