Sodium Hydroxide → HCID 19004305, compound

HRID 2225709Notes

Reaction equation

HRID 2225709 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[CH:28]=[CH:27][C:26]3[C:17](=[CH:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=2)=[CH:7][CH:6]=1.[OH-].[Na+]>O1CCCC1.O>[CH:16]1[C:17]2[C:26](=[CH:25][C:24]3[C:19]([CH:18]=2)=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:27]=[CH:28][C:15]=1[O:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:29])[C:3]([OH:30])=[O:2])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 53889920HCID 53889920, compound

Product 1

HCID 19004305HCID 19004305, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[[2-(2-anthracenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.615 g) in hot tetrahydrofuran (100 mL) was treated with 1N sodium hydroxide (4 mL) and diluted with water. The resulting solids were recovered by filtration and stirred in a mixture of dichloromethane and excess 2N hydrochloric acid until the solids dissolved. The organic layer was separated, dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from acetone-hexane gave 0.45 g of 4-[[2-(2-anthracenyloxy) ethyl]oxy]-alpha-oxobenzene-acetic acid as a colorless solid, mp 213°-214° C.

Workup

  1. filtrationThe resulting solids were recovered by filtration
  2. dissolutiondissolved
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customCrystallization from acetone-hexane

Sources & evidence

ORD record
ord-39d5b2ff2fb343b2b7654d50f656658e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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