Sodium Hydroxide → HCID 19004376, compound

HRID 2225713Notes

Reaction equation

HRID 2225713 reaction equation
C[O:2][C:3](=[O:26])[C:4](=[O:25])[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[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[O:25]=[C:4]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[CH:16]=2)=[CH:9][CH:10]=1)[C:3]([OH:26])=[O:2]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53675400HCID 53675400, compound

Product 1

HCID 19004376HCID 19004376, compoundYield 77.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of alpha-oxo-4-[[2-(5,6,7,8-tetrahydro-2-naphthalenyloxy)ethyl]oxy]benzeneacetic acid methyl ester (0.75 g) in hot methanol (10 mL) plus enough tetrahydrofuran to dissolve all solids, was treated with 1N sodium hydroxide (4 mL) and diluted with water. The organic solvent was removed under vacuum and the residue was mixed with water, acidified with excess hydrochloric acid, and extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from diethyl ether-hexane provided 0.56 g of alpha-oxo-4-[[2-(5,6,7,8-tetrahydro-2-naphthalenyloxy)ethyl]oxy]benzeneacetic acid as a colorless solid, mp 144°-145° C.

Workup

  1. dissolutionto dissolve all 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 diethyl ether-hexane

Sources & evidence

ORD record
ord-b39f54787bcf48e08e744ae978ce1176
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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