Benzyl 4-Hydroxybenzoate → Benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoate

HRID 382914Notes

Reaction equation

HRID 382914 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.[K].[OH:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[CH:23][CH:22]=1>CS(C)=O>[N+:16]([C:10]1[CH:11]=[CH:12][C:13]([O:20][C:21]2[CH:36]=[CH:35][C:24]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[CH:23][CH:22]=2)=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 5462222PotassiumHCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Product 1

HCID 18459341Benzyl 4-(4-nitro-3-benzyloxyphenoxy)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

24.7 g of 5-fluoro-2-nitrophenyl benzyl ether (0.1 mol) are dissolved in 250 ml of dimethyl sulfoxide, and a solution of 26.6 g of the potassium salt of benzyl 4-hydroxybenzoate (0.1 mol) in 250 ml of dimethyl sulfoxide is then slowly added drop wise with stirring at room temperature. The mixture is then stirred first at room temperature for 1 hour and then at 50° C. for 24 hours. The reaction solution is then allowed to cool to room temperature and is filtered through a fluted filter, the filtrate is diluted with 700 ml of water, and the crude product is extracted by shaking with 300 ml of ethyl acetate. The organic phase is then washed three times with water, dried over sodium sulfate and evaporated in a rotary evaporator until the reaction product precipitates out. The reaction product is stirred in petrol ether (boiling range 40 to 60° C.) for 2 hours, filtered off via a Büchner funnel and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 91%).

Workup

  1. stirringThe mixture is then stirred first at room temperature for 1 hour
  2. temperatureto cool to room temperature
  3. filtrationis filtered through
  4. filtrationa fluted filter
  5. additionthe filtrate is diluted with 700 ml of water
  6. extractionthe crude product is extracted
  7. stirringby shaking with 300 ml of ethyl acetate
  8. washThe organic phase is then washed three times with water
  9. dry with materialdried over sodium sulfate
  10. customevaporated in a rotary evaporator until the reaction product
  11. customprecipitates out
  12. stirringThe reaction product is stirred in petrol ether (boiling range 40 to 60° C.) for 2 hours
  13. filtrationfiltered off via a Büchner funnel
  14. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  15. customdrying cabinet (yield: 91%)

Sources & evidence

ORD record
ord-a7af881053fc4d46b7e860340c0b6398
Source dataset
uspto-grants-2001_10
Patent number
US06310238B1

Reaction notes

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