Benzene → HCID 57725029, compound

HRID 1987778Notes

Reaction equation

HRID 1987778 reaction equation
[N+:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][CH3:19])([CH3:16])[CH2:8][CH:7]2O)([O-:3])=[O:2].C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[N+:1]([C:4]1[C:5]([CH3:21])=[C:6]2[C:11](=[C:12]([CH3:15])[C:13]=1[CH3:14])[O:10][C:9]([CH2:17][O:18][CH3:19])([CH3:16])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 23118277HCID 23118277, compound

Product 1

HCID 57725029HCID 57725029, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10.1 g of 6-nitro-4-hydroxy-2-methoxymethyl-2,5,7,8-tetramethylchroman, 200 ml of benzene was added and 1.0 g of p-toluenesulfonic acid was added, followed by heating at reflux for 2 hours using a Dean-Stark apparatus. The reaction solution was poured into water and then extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution, washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, 9.4 g of the objective oily compound was obtained.

Workup

  1. temperatureby heating
  2. temperatureat reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing magnesium sulfate
  8. filtrationby filtration
  9. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-70ea1098134b4da5803b1fad1eec62f6
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

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