Dimethyl Sulfoxide → HCID 23312628, compound

HRID 745445Notes

Reaction equation

HRID 745445 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([CH:13]=1)[O:7][CH:8]([CH3:12])[C:9]([OH:11])=[O:10].[OH-].[Na+].CS(C)=[O:21]>O>[OH:21][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([CH:13]=1)[O:7][CH:8]([CH3:12])[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 16775830HCID 16775830, compound

Product 1

HCID 23312628HCID 23312628, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5 Grams (21.8 moles) of 2-(5-fluoro-2-nitrophenoxy)propionic acid was heated for two hours with 5 ml of 25 percent (by weight) aqueous sodium hydroxide and 100 ml of DMSO and allowed to stand overnight. The mixture was diluted with water and extracted with 1,1,1-trichloroethane (organic discarded), then with ether. The aqueous layer was acidified and extracted with ether. The ether solution was stripped to give 2.5 g of solid product which was recrystallized from ethanol/chloroform to give 1.7 g (35 percent) of the desired product. M.P.=190°-195° C. NMR and IR spectra supported the identification.

Workup

  1. extractionextracted with 1,1,1-trichloroethane (organic discarded)
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-c987ed37f0e84a8796756fac261a0289
Source dataset
uspto-grants-1986_07
Patent number
US04599105

Reaction notes

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