Acetic Acid → HCID 13796211, compound

HRID 1277514Notes

Reaction equation

HRID 1277514 reaction equation
C[O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:6]([O:7]C)=[CH:5][C:4]=1[CH:14]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:15].C(O)(=O)C.Br>O>[CH:14]([C:4]1[CH:5]=[C:6]([OH:7])[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:3]=1[OH:2])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 23454195HCID 23454195, compound

Product 1

HCID 13796211HCID 13796211, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.0 g of 2-sec-octadecyl-5-nitrohydroquinone dimethyl ether and 135 ml of glacial acetic acid were added 15 ml of 47% hydrobromic acid and the mixture was heated with reflux for 10 hours. After being allowed to cool, the mixture was added to water and then extracted with ether. After washing with water and drying, the solvent was distilled off under reduced pressure and the residue was purified through silica gel column chromatography. As the developing solvent,benzene/n-hexane (1:1) was used. The end product was obtained in 1.7 g as yellowish brown semisolid. The structure was determined by means of IR, NMR and elemental analysis data. Elemental analysis:

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 10 hours
  3. temperatureto cool
  4. extractionextracted with ether
  5. washAfter washing with water
  6. customdrying
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified through silica gel column chromatography
  9. customThe end product was obtained in 1.7 g as yellowish brown semisolid

Sources & evidence

ORD record
ord-0232868ec3fd4553901d9cb65d2a4626
Source dataset
uspto-grants-1981_07
Patent number
US04277553

Reaction notes

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