Sodium Hydroxide → HCID 54091624, compound

HRID 2225746Notes

Reaction equation

HRID 2225746 reaction equation
C[O:2][C:3](=[O:27])[C:4](=[O:26])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH2:13][CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[O:12])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O1CCCC1.O>[CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:24]=[CH:25][C:16]=1[O:15][CH2:14][CH2:13][S:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:26])[C:3]([OH:27])=[O:2])=[CH:6][CH:7]=1)=[O:12]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53828882HCID 53828882, compound

Product 1

HCID 54091624HCID 54091624, compoundYield 72.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of rac.-4-[[2-(2-naphthalenyloxy)ethyl]sulfinyl]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in hot methanol (5 mL) and sufficient tetrahydrofuran to dissolve the solids was treated with 1N sodium hydroxide (2.0 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 acetone-hexane provided 0.35 g of rac.-4-[[2-(2-naphthalenyloxy) ethyl]sulfinyl]-alpha-oxobenzeneacetic acid as a yellow solid, mp 157°-158° 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
  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-ea26d4411d31498dbdedc6b5e2ec6cd3
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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