1,2,3,5-Tetrahydroxybenzene → HCID 14446594, compound

HRID 567200Notes

Reaction equation

HRID 567200 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:9])[C:3]=1[OH:10].[Cl-].[Al+3].[Cl-].[Cl-].[C:15](Cl)(=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18].Cl>[N+](C1C=CC=CC=1)([O-])=O.O>[OH:1][C:2]1[C:3]([OH:10])=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[C:7]=1[C:15]([CH2:16][CH:17]([CH3:19])[CH3:18])=[O:20]

Participants

7

Reactant 4

HCID 121,2,3,5-TetrahydroxybenzeneHCID 313Hydrochloric AcidHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14446594HCID 14446594, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7416NitrobenzeneSolvent

Procedure

Under an atmosphere of argon, 4.28 g (30.14 mmol) of 1,2,3,5-tetrahydroxybenzene (3) was dissolved by stirring in 70 ml of nitrobenzene. The solution was cooled with water. To the cold solution, 16.1 g (120.56 mmol, 4.00 equivalents) of granular aluminum chloride was added piecemeal and stirred. To the stirred mixture, 3.67 ml (30.1 mmol, 1.00 equivalent) of isovaleryl chloride was added dropwise. After 5 hours, the reaction solution was poured into 100 ml of a cold.2 M hydrochloric acid solution, stirred for 20 minutes, and extracted from ether. The organic layer was washed with water, distilled to remove ether, combined with a large volume of water, and distilled under reduced pressure to remove nitrobenzene. The residue was extracted from ether, washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to obtain a crude reaction product. By purifying the crude product by silica gel column chromatography (300 g of Wako Gel C-200, hexane:ethyl acetate=2:1), 1.85 g (yield 27.2%) of the product (9) was obtained in the form of yellow powder crystals.

Workup

  1. additionthe reaction solution was poured into 100 ml of a cold
  2. extractionextracted from ether
  3. washThe organic layer was washed with water
  4. distillationdistilled
  5. customto remove ether
  6. distillationdistilled under reduced pressure
  7. customto remove nitrobenzene
  8. extractionThe residue was extracted from ether
  9. washwashed with saturated brine
  10. dry with materialdried over sodium sulfate
  11. distillationdistilled under a reduced pressure
  12. customto obtain a crude
  13. customreaction product
  14. customBy purifying the crude product by silica gel column chromatography (300 g of Wako Gel C-200, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-eda0a271b54043738ec0c7758e8ca8c3
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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