Sodium Hydroxide → HCID 19004301, compound

HRID 2225719Notes

Reaction equation

HRID 2225719 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:24]([O:25][CH2:26][CH2:27][OH:28])=[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>[OH:28][CH2:27][CH2:26][O:25][C:24]1[C:15]([O:14][CH2:13][CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:29])[C:3]([OH:30])=[O:2])=[CH:10][CH:9]=2)=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 67757305HCID 67757305, compound

Product 1

HCID 19004301HCID 19004301, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-[[2-[3-(2-hydroxyethoxy)-2-naphthalenyloxy]ethyl]oxy]-alphaoxobenzeneacetic acid methyl ester (0.6 g) in hot methanol (10 mL) plus enough tetrahydrofuran to dissolve the 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 2 N hydrochloric acid, and extracted with dichloromethane-tetrahydrofuran. The organic layer was dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from acetone-hexane provided 0.4 g of 4-[[2-[3-(2-hydroxyethoxy)-2-naphthalenyloxy]ethyl]oxy]-alpha-oxobenzeneacetic 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-tetrahydrofuran
  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-0646bd0e73df4c8e82f3b7e74ba8859e
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…