1,2,3,5-Tetrahydroxybenzene → HCID 85756659, compound

HRID 567199Notes

Reaction equation

HRID 567199 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:19])[CH:16]([CH3:18])[CH3:17].Cl>[N+](C1C=CC=CC=1)([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]([CH:16]([CH3:18])[CH3:17])=[O:19]

Participants

6

Reactant 4

HCID 121,2,3,5-TetrahydroxybenzeneHCID 313Hydrochloric AcidHCID 62325Isobutyryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 85756659HCID 85756659, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent2×

Procedure

In a vessel fitted with a calcium chloride tube, 1.00 g (7.04 mmol) of 1,2,3,5-tetrahydroxybenzene (3) was dissolved in 20 ml of nitrobenzene and stirred. Into the stirred mixture, 2.82 g (21.1 mmol, 3.00 equivalents) of granular aluminum chloride was added piecemeal and stirred. One hour thereafter, a nitrobenzene (5.0 ml) solution of 0.750 g (7.04 mmol, 1.00 equivalent) of isobutyryl chloride was added dropwise. Ten hours thereafter, the reaction solution was poured into 100 ml of cold 2 M hydrochloric acid solution, stirred for 30 minutes, and then extracted from ether. The ether layer was washed with water, distilled to remove ether, combined with a large volume of water, and distilled water under reduced pressure to remove nitrobenzene by steam distillation. The residue was extracted from ether, washed with saturated brine, dried over sodium sulfate, and distilled under a reduced pressure to remove the solvent and obtain 1.38 g of crude product. By purifying the crude product by column chromatography (SiO2, 20 g of Wako Gel C-300, hexane:ether=1:1), 441 mg (yield 65.9%) of the product (8) was obtained in the form of yellow powder crystals.

Workup

  1. customIn a vessel fitted with a calcium chloride tube
  2. stirringstirred
  3. stirringstirred for 30 minutes
  4. extractionextracted from ether
  5. washThe ether layer was washed with water
  6. distillationdistilled
  7. customto remove ether
  8. distillationdistilled water under reduced pressure
  9. customto remove nitrobenzene
  10. distillationby steam distillation
  11. extractionThe residue was extracted from ether
  12. washwashed with saturated brine
  13. dry with materialdried over sodium sulfate
  14. distillationdistilled under a reduced pressure
  15. customto remove the solvent
  16. customobtain 1.38 g of crude product
  17. customBy purifying the crude product by column chromatography (SiO2, 20 g of Wako Gel C-300, hexane:ether=1:1)

Sources & evidence

ORD record
ord-8c184a8ed48c4332a414351861430fa8
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

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