Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 2,3-Difluoro-6-nitro-[(2-hydroxypropyl)oxy]benzene

HRID 1034036Notes

Reaction equation

HRID 1034036 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:13][CH:14]([O:16]C1CCCCO1)[CH3:15].S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:12][CH2:13][CH:14]([OH:16])[CH3:15]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 146971782,3-Difluoro-6-nitro{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene

Product 1

HCID 146971862,3-Difluoro-6-nitro-[(2-hydroxypropyl)oxy]benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6.35 g of 2,3-difluoro-6-nitro-{[2-(tetrahydropyran-2-yl)oxypropyl]oxy}benzene (I, Xa=Xb=F, Rc=THP), 60 ml of anhydrous ethanol and 640 mg of pyridinium tosylate was stirred at room temperature overnight and then heated under refluxing for 1 hour. The solvent was removed under reduced pressure. To the residue were added ethyl acetate and 1 N hydrochloric acid. The mixture was shaken, and the organic layer was separated. The organic layer was washed successively with a saturated sodium bicarbonate aqueous solution and water, then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to yield the oily titled compound. This product was used in the following reaction without purification.

Workup

  1. temperatureheated
  2. temperatureunder refluxing for 1 hour
  3. customThe solvent was removed under reduced pressure
  4. additionTo the residue were added ethyl acetate and 1 N hydrochloric acid
  5. stirringThe mixture was shaken
  6. customthe organic layer was separated
  7. washThe organic layer was washed successively with a saturated sodium bicarbonate aqueous solution and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-090ce16f32c04f7983ae84473edee969
Source dataset
uspto-grants-1994_05
Patent number
US05312999

Reaction notes

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