Tetrahydrofuran → HCID 19004274, compound

HRID 2225722Notes

Reaction equation

HRID 2225722 reaction equation
C[O:2][C:3](=[O:12])[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-:13].[Na+].[O:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>CO.O>[OH:15][C:19]1[C:18]([O:13][CH2:4][CH2:3][O:2][C:8]2[CH:9]=[CH:10][C:5]([C:4](=[O:11])[C:3]([OH:2])=[O:12])=[CH:6][CH:7]=2)=[CH:17][C:16]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[CH:10][CH:9]=2

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 84835Methyl phenylglyoxalate

Product 1

HCID 19004274HCID 19004274, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-[[2-(3-hydroxy)-2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.065 g) in hot methanol (2 mL) plus tetrahydrofuran (5 mL) was treated with 1N sodium hydroxide (0.5 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 dichloromethane-diethyl ether provided 0.055 g of 4-[[2-(3-hydroxy-2-naphthalenyloxy) ethyl]oxy]-alpha-oxobenzeneacetic acid as a colorless solid, mp 191°-192° C.

Workup

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

Sources & evidence

ORD record
ord-862e333ca9bd42fa86bc2e796c3e6b84
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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