1-Benzyloxy-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene → 3-(Prop-2-enyloxy)-4-nitro-2,5,6-trifluorophenol

HRID 430050Notes

Reaction equation

HRID 430050 reaction equation
C([O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([N+:17]([O-:19])=[O:18])=[C:11]([O:20][CH2:21][CH:22]=[CH2:23])[C:10]=1[F:24])C1C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:21]([O:20][C:11]1[C:10]([F:24])=[C:9]([OH:8])[C:14]([F:15])=[C:13]([F:16])[C:12]=1[N+:17]([O-:19])=[O:18])[CH:22]=[CH2:23]

Participants

3

Reactant 1

HCID 183538391-Benzyloxy-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene

Product 1

HCID 183538423-(Prop-2-enyloxy)-4-nitro-2,5,6-trifluorophenol

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

33.9 g of the 1-benzyloxy-3-(prop-2-enyloxy)-4-nitro-2,5,6-trifluorobenzene prepared as described in Example 5 (0.1 mol) are dissolved in 120 ml of trifluoroacetic acid in a three-neck flask fitted with reflux condenser and stirrer, and the mixture is then refluxed for 4 hours. The reaction solution is then allowed to cool to room temperature, and the crude product is extracted by shaking with 200 ml of ethyl acetate and 300 ml of water. The organic phase is washed three times with water, dried over sodium sulfate and evaporated to half in a rotary evaporator. The precipitated reaction product is then recrystallized from a mixture of n-hexane and methylene chloride (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.

Workup

  1. customfitted
  2. temperaturewith reflux condenser and stirrer
  3. temperaturethe mixture is then refluxed for 4 hours
  4. extractionthe crude product is extracted
  5. washThe organic phase is washed three times with water
  6. dry with materialdried over sodium sulfate
  7. customevaporated to half in a rotary evaporator
  8. customThe precipitated reaction product
  9. customis then recrystallized from a mixture of n-hexane and methylene chloride (volume ratio 1:1)
  10. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  11. customdrying cabinet

Sources & evidence

ORD record
ord-77e155cb2d54421189303d70508312e2
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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