Water → 3-(Benzyloxy)-4-nitrophenol

HRID 430047Notes

Reaction equation

HRID 430047 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](F)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:19].[K+].O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([OH:19])[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium Hydroxide2×HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 109777113-(Benzyloxy)-4-nitrophenol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

39.5 g of the 2-benzyloxy-4-fluoronitrobenzene (0.16 mol) prepared as described in Example 1 are added to a mixture of an aqueous potassium hydroxide solution prepared from 27.2 g of potassium hydroxide (0.48 mol) and 180 ml of distilled water, and 150 ml of dimethyl sulfoxide in a three-neck flask fitted with reflux condenser, stirrer and nitrogen inlet, and the mixture is then heated to 100° C. After 4 hours, the reaction solution is allowed to cool to room temperature, and the residue is filtered off via a fluted filter. The dark-orange solution is then added to 800 ml of water, and concentrated hydrochloric acid is added with vigorous stirring until the mixture is acidic. Within about 1 hour, a white-yellowish, flaky reaction product precipitates; this is filtered off via a Büchner funnel and washed three times with water. The reaction product is recrystallized from ethanol 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, stirrer and nitrogen inlet
  3. temperatureto cool to room temperature
  4. filtrationthe residue is filtered off via
  5. filtrationa fluted filter
  6. additionThe dark-orange solution is then added to 800 ml of water, and concentrated hydrochloric acid
  7. additionis added
  8. waitWithin about 1 hour
  9. customa white-yellowish, flaky reaction product precipitates
  10. filtrationthis is filtered off via a Büchner funnel
  11. washwashed three times with water
  12. customThe reaction product is recrystallized from ethanol
  13. customdried for 48 hours under nitrogen at 40 ° C./10 mbar in a vacuum
  14. customdrying cabinet

Sources & evidence

ORD record
ord-6fd68201551e465386fb626a4d7c242e
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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