2,6-Di-tert-butylphenol → HCID 15027745, compound

HRID 2254107Notes

Reaction equation

HRID 2254107 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22](Cl)=[O:23])[CH:18]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C(=S)=S>[CH3:12][C:11]([C:7]1[CH:8]=[C:9]([C:22]([C:19]2[CH:18]=[C:17]([CH3:16])[O:21][N:20]=2)=[O:23])[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]=1[OH:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 314052,6-Di-tert-butylphenolHCID 27368945-Methylisoxazole-3-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15027745HCID 15027745, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 20.6 g (0.1 mole) of 2,6-di-tert-butylphenol and 15.6 g (0.107 mole) of 5-methylisoxazole-3-carboxylic acid chloride in 100 mL of CS2 is added 14.3 g (0.107 mole) of AlCl3 at +5° C. Vigorous stirring is maintained at that temperature for 1 hour and then at room temperature for 1 hour. The CS2 is decanted off and the residue treated with 350 mL of ice cold IN HCl and extracted with Et2O. The extracts are washed with saturated NaHCO3 solution and brine, dried with Na2SO4 and evaporated to give a mixture of products. The desired product is separated by flash chromatography (0% to 50% CH2Cl2 /n hexane) on silica gel to give 4.4 g of the crude ketone which is recrystallized from n-pentane to give 2.3 g (14%) of pale yellow crystals, [3,5-bis(1,1 dimethylethyl)-4 -hydroxyphenyl(5-methyl-3-isoxazolyl)methanone, mp 120° C.; 1H NMR (CDCl3)δ1.48 (s, 18H, tert-butyl), 2.52 (s, 3H, CH3), 5.85 (s, 1H, OH), 6.48 (s, 1H, isoxazole aromatic), 8.23 (s, 2H, phenyl aromatics); IR (KBr) 1590, 1600, 1650, 3600 cm-1 ; MS (DEI) m/e 315 (M+), 300 (M-CH3).

Workup

  1. temperatureis maintained at that temperature for 1 hour
  2. customThe CS2 is decanted off
  3. additionthe residue treated with 350 mL of ice cold IN HCl
  4. extractionextracted with Et2O
  5. washThe extracts are washed with saturated NaHCO3 solution and brine
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customto give
  9. additiona mixture of products
  10. customThe desired product is separated by flash chromatography (0% to 50% CH2Cl2 /n hexane) on silica gel

Sources & evidence

ORD record
ord-bc3c3931730b43838d8b24d1eb1dd526
Source dataset
uspto-grants-1993_08
Patent number
US05234937

Reaction notes

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