Potassium Hydroxide → Phenol, 2-chloro-4-fluoro-5-nitro-

HRID 846504Notes

Reaction equation

HRID 846504 reaction equation
[OH-].[K+].CC1C=CC(S([O:13][C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[C:17]([F:23])=[CH:16][C:15]=2[Cl:24])(=O)=O)=CC=1[N+]([O-])=O>O.O1CCOCC1>[Cl:24][C:15]1[CH:16]=[C:17]([F:23])[C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=1[OH:13]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19882798HCID 19882798, compound

Product 1

HCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-Yield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 12.84 g (0.195 mole) of potassium hydroxide in 200 mL of water was added to a vigorously stirred solution of 34.0 g (0.097 mole) of 2-chloro-4-fluoro-5-nitrophenyl 4-methyl-3-nitrophenylsulfonate in 190 mL of p-dioxane. The resultant mixture was stirred at room temperature for approximately 18 hours. The reaction mixture was filtered and the filtrate acidified with concentrated hydrochloric acid. The acidic solution was extracted with diethyl ether. The ether extract was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated under reduced pressure to leave a solid. The solid was washed with petroleum ether to yield 15.07 g of 2-chloro-4-fluoro-5-nitrophenol.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionThe acidic solution was extracted with diethyl ether
  3. extractionThe ether extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customto leave a solid
  8. washThe solid was washed with petroleum ether

Sources & evidence

ORD record
ord-0591c3e9f1a4449a801790f5a509d527
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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