Hydrochloric Acid → HCID 54109422, compound

HRID 567209Notes

Reaction equation

HRID 567209 reaction equation
[H-].[C:2]1([OH:10])[CH:9]=[C:7]([CH3:8])[CH:6]=[C:4]([OH:5])[CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[C:15](Cl)(=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18].Cl>C1C=CC=CC=1.C(=S)=S.O>[CH3:18][CH:17]([CH3:19])[CH2:16][C:15]([C:9]1[C:7]([CH3:8])=[CH:6][C:4]([OH:5])=[CH:3][C:2]=1[OH:10])=[O:20]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 66054Isovaleryl chlorideHCID 6451240Aluminum(III) ChlorideHCID 70222055HCID 70222055, compound

Product 1

HCID 54109422HCID 54109422, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6348Carbon DisulfideSolvent

Procedure

Orcinol monohydride, 14.20 g (100.0 mmol), in 160 ml of benzene was heated to distill benzene. This step was carried out twice by way of an operation of dehydration. The product of dehydration was dissolved in 45 ml of nitrobenzene and 45 ml of carbon disulfide, and 26.7 g (200 mmol, 2.00 equivalents) of aluminum chloride was added piecemeal while cooled with cold water and stirred, with a calcium chloride tube attached. Then, 12.1 g (100 mmol, 1.00 equivalent) of isovaleryl chloride was slowly added dropwise and stirred at room temperature for 14 hours. After the stop of the evolution of an acidic gas was confirmed, the resultant reaction mixture was poured into dilute hydrochloric acid (prepared from 100 ml of concentrated hydrochloric acid and 400 ml of cold water), stirred, and then extracted by ether. The ether layer was washed with saturated brine and the ether was removed under a reduced pressure. The residue was combined with water added piecemeal and meanwhile distilled under a reduced pressure to remove nitrobenzene by steam distillation. The residue was extracted by ether, washed with saturated brine, dried over sodium sulfate, and distilled off the solvent and obtain 18.53 g of a crude product in the form of brown viscous oily substance. The crude product was subjected to silica gel column chromatography (220 g of Wako Gel C-200, eluted with hexane:ethyl acetate=9:1) to obtain 5.681 g of (2,4-dihydroxy-6-methylphenyl) (2-methylpropyl) ketone (47).

Workup

  1. distillationto distill benzene
  2. dissolutionThe product of dehydration was dissolved in 45 ml of nitrobenzene
  3. stirringstirred at room temperature for 14 hours
  4. customthe resultant reaction mixture
  5. stirringstirred
  6. extractionextracted by ether
  7. washThe ether layer was washed with saturated brine
  8. customthe ether was removed under a reduced pressure
  9. distillationmeanwhile distilled under a reduced pressure
  10. customto remove nitrobenzene
  11. distillationby steam distillation
  12. extractionThe residue was extracted by ether
  13. washwashed with saturated brine
  14. dry with materialdried over sodium sulfate
  15. distillationdistilled off the solvent
  16. customobtain 18.53 g of a crude product in the form of brown viscous oily substance
  17. washThe crude product was subjected to silica gel column chromatography (220 g of Wako Gel C-200, eluted with hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8860c348f1ba4aa6abaa86b19cbbe28f
Source dataset
uspto-grants-2001_01
Patent number
US06177474B1

Reaction notes

Loading…