Sodium Hydroxide → HCID 19004270, compound

HRID 2225711Notes

Reaction equation

HRID 2225711 reaction equation
C[O:2][C:3](=[O:30])[C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:16]3[C:21]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[CH:28]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7][CH:6]=1.[OH-].[Na+]>O1CCCC1.O>[O:29]=[C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[C:16]3[C:21]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=4[CH:28]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:7][CH:6]=1)[C:3]([OH:30])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53855057HCID 53855057, compound

Product 1

HCID 19004270HCID 19004270, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of alpha-oxo-4-[[2-(9-phenanthrenyloxy)ethyl]oxy]benzeneacetic acid methyl ester (0.685 g) in hot tetrahydrofuran (100 mL) was treated with 1N sodium hydroxide (4 mL) and diluted with water. The organic solvent was removed under vacuum and the aqueous solution was acidified with excess 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-(9-phenanthrenyloxy) ethyl]oxy]benzeneacetic acid as a colorless solid, mp 179°-180° C.

Workup

  1. customThe organic solvent was removed under vacuum
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give crude product
  7. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-aa9ed33f1b584687bf6c04a68bd3ee40
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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