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Chemical Structure| 19263-36-6 Chemical Structure| 19263-36-6

Structure of 19263-36-6

Chemical Structure| 19263-36-6

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Product Details of [ 19263-36-6 ]

CAS No. :19263-36-6
Formula : C16H24O
M.W : 232.36
SMILES Code : OC1=C(C(C)(C)C)C=C(C=C)C=C1C(C)(C)C
MDL No. :MFCD28505064
InChI Key :ZMRCFZFFKWFWSK-UHFFFAOYSA-N
Pubchem ID :12576680

Safety of [ 19263-36-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 19263-36-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 19263-36-6 ]

[ 19263-36-6 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 24457-08-7 ]
  • [ 19263-36-6 ]
YieldReaction ConditionsOperation in experiment
2.094 g (90.2%) Example 13 Synthesis of 2,6-di-tert-butyl-4-vinyl-phenol (12). A solution of 3,5-di-tert-butyl-4-hydroxycinnamic acid (2.77 g, 10 mmol) in dry DMF (20 mL) was refluxed at 150° C. under N2 for 2 h with stirring. The resulting mixture was then poured into water (200 mL) and extracted with chloroform (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluding with hexane, to give 2.094 g (90.2percent) of the title compound as a colorless solid: mp 51-51.5° C.; NMR (400 MHz, CDCl3): delta 7.248 (s, 2H), 6.666 (d*d, 1H, J1=10.8 Hz, J2=17.6 Hz), 5.587 (d, 1H, J=16.8 Hz), 5.241 (s, 1H), 5.094 (d, 1H, J=10.8 Hz), 1.456 (s, 18H); 13C NMR (100 MHz, CDCl3): delta 153.980, 137.529, 136.055, 129.040, 123.216, 110.996, 34.565, 30.507; Anal. Calcd. for C16H24O: C, 82.70; H, 10.41. Found; C, 83.08; H, 10.37.
  • 4
  • [ 865087-55-4 ]
  • [ 19263-36-6 ]
  • [ 865087-47-4 ]
  • 5
  • [ 865087-56-5 ]
  • [ 19263-36-6 ]
  • [ 865087-47-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; triphenylphosphine;palladium diacetate; Example 14 Synthesis of 2,6-di-tert-butyl-4-{2-[4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-vinyl}-phenol (13). A flame-dried sealable Schlenk tube was charged with 11 (1.69 g, 5.0 mmol), 12 (2.32 g, 10.0 mmol), Pd(OAc)2 (112 mg, 0.50 mmol), and PPh3 (131 mg, 0.50 mmol), evacuated, and then backfilled with N2. Next, dry Et3N (10 mL) was added under an N2 flow. The Schlenk tube was next sealed, the mixture was degassed by 3 freeze-thaw cycles, and backfilled with N2. The Schlenk tube was then wrapped with aluminum foil and stirred at 100° C. for 36 h. The reaction mixture was then cooled to room temperature, diluted with methylene chloride (50 mL), filtered through a thin pad of silica gel, and concentrated in vacuo to afford a red solid. The crude product was purified by flash chromatography on silica gel, eluding with 3:1 hexane:ethyl acetate to give the title compound 2.01 g (91.2percent) as a colorless solid: mp 234-235° C.; 1H NMR (400 MHz, CDCl3): delta 8.402 (s, 2H), 7.371 (s, 2H), 7.307 (s, 2H), 7.133 (d, 1H, J=16.4 Hz), 6.936 (d, 1H, J=16.0 Hz), 5.331 (s, 1H), 1.951 (s, 6H), 1.911 (s, 6H), 1.499 (s, 18H); 13C NMR (100 MHz, CDCl3): delta 153.971, 148.630, 148.502, 137.347, 136.301, 135.928, 134.817, 131.251, 129.595, 128.876, 125.837, 125.709, 123.598, 34.638, 30.534, 19.997, 16.822; HRMS (EI): m/z 441.3023 [M+]; calcd, 441.3032; Anal. Calcd. for C31H39NO.H2O: C, 81.00; H, 8.99; N, 3.05. Found; C, 81.01; H, 8.64; N, 3.02.
  • 6
  • [ 865087-54-3 ]
  • [ 19263-36-6 ]
  • [ 865087-47-4 ]
  • 7
  • [ 22014-01-3 ]
  • [ 19263-36-6 ]
  • 9
  • [ 19263-36-6 ]
  • 2,6-di-tert-butyl-4-{2-[4-(3,5-dimethyl-1-octyl-1H-pyridin-4-ylidene)-3,5-dimethyl-cyclohexa-2,5-dienylidene]-ethylidene}-cyclohexa-2,5-dienone [ No CAS ]
  • 10
  • [ 19263-36-6 ]
  • 4-{4-[2-(3,5-di-<i>tert</i>-butyl-4-hydroxy-phenyl)-vinyl]-2,6-dimethyl-phenyl}-3,5-dimethyl-1-octyl-pyridinium; iodide [ No CAS ]
  • 11
  • [ 719-22-2 ]
  • [ 19263-36-6 ]
  • 12
  • [ 67-56-1 ]
  • [ 7050-91-1 ]
  • [ 19263-36-6 ]
YieldReaction ConditionsOperation in experiment
With pyridine; hydrogenchloride;copper chromite; In 1,4-dioxane; hexane; A high pressure autoclave was charged with 100 grams (.403 mole) of 3,5-di-t-butyl-4-hydroxyacetophenone, 500 milliliters of dioxane and 10 grams of copper chromite catalyst. Pressure was raised to 1000 psi, and the mixture was heated to 125° to 135° C. until no more hydrogen was absorbed. The mixture was cooled, the catalyst filtered off and the solvent removed to obtain 96 grams of carbinol with a 95 percent yield and a melting point of 86° to 88° C. The carbinol was quantitatively converted to the 2,6-di-t-butyl-4-(alpha-chloro)ethylphenol by vigorous stirring of 50 grams (0.20 mole) of the carbinol dissolved in 100 milliliters of hexane with 100 milliliters of concentrated HCl for one hour at room temperature. The hexane layer was separated and the solvent removed. The residue was used in the final step. To the residue of 2,6-di-t-butyl-4-(alpha-chloro)ethylphenol was added 100 milliliters of pyridine. This solution was refluxed for 30 minutes. The pyridine was then removed by the vacuum distillation. The residue was washed thoroughly with water, then dissolved in a small amount of acetone and recrystallized at -78° C. to obtain 44 grams of 2,6-di-t-butyl-4-vinylphenol with a 95 percent yield of a melting point of 36 to 39° C.
  • 13
  • [ 19263-36-6 ]
  • [ 542-92-7 ]
  • exo-2,6-di-tert-butyl-4-(bicyclo[2.2.1]hept-5-en-2-yl)phenol [ No CAS ]
  • endo-2,6-di-tert-butyl-4-(bicyclo[2.2.1]hept-5-en-2-yl)phenol [ No CAS ]
 

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