3279-27-4

Usage

Uses

Flavors, Fragrances, Antioxidant Intermediates

InChI:InChI=1/C11H16O/c1-4-11(2,3)9-7-5-6-8-10(9)12/h5-8,12H,4H2,1-3H3

Synthetic route

2-methyl-but-2-ene (513-35-9) + phenol (108-95-2) → tert-amylphenol (3279-27-4)

Conditions	Yield
With trichlorophosphate
With aluminium(III) phenoxide

2-methyl-2-butylchloride (594-36-5) + phenol (108-95-2) → tert-amylphenol (3279-27-4)

Conditions	Yield
With aluminium trichloride at 20 - 100℃;

2-Methyl-1-butene (563-46-2) + phenol (108-95-2) → tert-amylphenol (3279-27-4)

Conditions	Yield
With diphenyl hydrogen phosphate

4-t-amylphenol (80-46-6) → tert-amylphenol (3279-27-4)

Conditions	Yield
In neat (no solvent) at 99.9 - 209.9℃; Equilibrium constant; effect of temperature;

2-methyl-but-2-ene (513-35-9) + phenol (108-95-2) → tert-amylphenol (3279-27-4) + 4-tert-pentyl-phenol, 2.4-di-tert-pentyl-phenol

Conditions	Yield
With sulfuric acid at 50℃;

tert-Amyl alcohol (75-85-4) + phenol (108-95-2) → tert-amylphenol (3279-27-4) + 4-t-amylphenol (80-46-6)

Conditions	Yield
With sulfated zirconia at 140℃; for 1h;

tert-amylphenol (3279-27-4) → tert-Amyl-o-Bromophenol

Conditions	Yield
With N-Bromosuccinimide; diisopropylamine In dichloromethane at 40℃; for 20h; Inert atmosphere;	92%
With N-Bromosuccinimide; diisopropylamine In dichloromethane for 16h; Inert atmosphere; Reflux;	81%
With N-Bromosuccinimide; diisopropylamine In dichloromethane Reflux;

tert-amylphenol (3279-27-4) + methyl iodide (74-88-4) → 2-methoxy-4-tert-pentylbenzene

Conditions	Yield
Stage #1: tert-amylphenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.666667h; Schlenk technique; Sealed tube; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil for 3h; Schlenk technique; Sealed tube;	70%

tert-amylphenol (3279-27-4) + 2-bromoethanol (540-51-2) → C13H20O2

Conditions	Yield
Stage #1: tert-amylphenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 2-bromoethanol With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 110℃; for 96h;	52%

tert-amylphenol (3279-27-4) → 2-hydroxy-3-tert-pentyl-benzaldehyde

Conditions	Yield
With hexamethylenetetramine durch Eintragen in ein zuvor auf 150-165grad erhitztes Gemisch von Glycerin und Borsaeure und anschliessendes Behandeln mit wss.H2SO4 unter Durchleiten von Wasserdampf;

tert-amylphenol (3279-27-4) → tert-pentyl-[1,4]benzoquinone-4-oxime

Conditions	Yield
With hydrogenchloride; sodium nitrite

tert-amylphenol (3279-27-4) → 2,4-dichloro-6-tert-pentyl-phenol (122269-08-3)

Conditions	Yield
With tetrachloromethane; chlorine

tert-amylphenol (3279-27-4) → 3.5-dinitro-2-hydroxy-1-tert-pentyl-benzene (87014-94-6)

Conditions	Yield
With tetrachloromethane; nitric acid at 40℃;

tert-amylphenol (3279-27-4) → 4-t-amylphenol (80-46-6)

Conditions	Yield
In neat (no solvent) at 99.9 - 209.9℃; Equilibrium constant; effect of temperature;

tert-amylphenol (3279-27-4) → cis-1-tert.-Pentyl-cyclohexanol-(2)

Conditions	Yield
With hydrogen; nickel In ethanol at 140 - 200℃; under 98800 - 129200 Torr;

tert-amylphenol (3279-27-4) + hexamethylenetetramine (100-97-0) + metaboric acid (13460-50-9) + glycerol (56-81-5) → 2-hydroxy-3-tert-pentyl-benzaldehyde

Conditions	Yield
at 165℃; anschliessendes Behandeln mit wss. H2SO4 bei 115grad;

tert-amylphenol (3279-27-4) → N,N'-bis-(2-hydroxy-3-tert-pentyl-benzyliden)-ethylenediamine

Conditions	Yield
Multi-step reaction with 2 steps 1: hexamethylenetetramine / durch Eintragen in ein zuvor auf 150-165grad erhitztes Gemisch von Glycerin und Borsaeure und anschliessendes Behandeln mit wss.H2SO4 unter Durchleiten von Wasserdampf View Scheme

tert-amylphenol (3279-27-4) → 2-tert-Pentylcyclohexanon (5441-54-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / ethanol / 140 - 200 °C / 98800 - 129200 Torr 2: Na2Cr2O7 View Scheme

tert-amylphenol (3279-27-4) → N-(2-diethylaminoethyl)-3-t-amylsalicylamide hydrochloride

Conditions	Yield
With sodium

4,4'-methylenebis(cyclohexyl urea) + tert-amylphenol (3279-27-4) → N,N'-(4,4'-methanediyl-dicyclohexyl)-di(carbamic acid (2-tert-amylphenyl) ester)

Conditions	Yield
at 230℃; under 262.526 Torr; Product distribution / selectivity; Industry scale;

tert-amylphenol (3279-27-4) → (2-bromo-6-(tert-pentyl)phenoxy)trimethylsilane (1334501-85-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; diisopropylamine / dichloromethane / 20 h / 40 °C / Inert atmosphere 2: triethylamine / toluene / 12 h / 50 °C / Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → 2-(tert-pentyl)-6-(trimethylsilyl)phenol (1334501-86-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; diisopropylamine / dichloromethane / 20 h / 40 °C / Inert atmosphere 2: triethylamine / toluene / 12 h / 50 °C / Inert atmosphere 3: n-butyllithium / hexanes; diethyl ether / 12 h / -78 - 20 °C / Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → 2-(tert-Pentyl)-6-(trimethylsilyl)phenyl trifluoromethanesulfonate (1334501-77-7)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; diisopropylamine / dichloromethane / 20 h / 40 °C / Inert atmosphere 2.1: triethylamine / toluene / 12 h / 50 °C / Inert atmosphere 3.1: n-butyllithium / hexanes; diethyl ether / 12 h / -78 - 20 °C / Inert atmosphere 4.1: n-butyllithium / hexanes; diethyl ether / -78 - 20 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → trimethyl(3-(2-methylbut-3-en-2-yl)phenyl)silane (1334501-78-8) + (8-ethyl-8-methylbicyclo[4.2.0]octa-1,3,5-trien-3-yl)trimethylsilane (1334501-79-9)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; diisopropylamine / dichloromethane / 20 h / 40 °C / Inert atmosphere 2.1: triethylamine / toluene / 12 h / 50 °C / Inert atmosphere 3.1: n-butyllithium / hexanes; diethyl ether / 12 h / -78 - 20 °C / Inert atmosphere 4.1: n-butyllithium / hexanes; diethyl ether / -78 - 20 °C / Inert atmosphere 4.2: 12 h / -78 - 20 °C / Inert atmosphere 5.1: tris-(dibenzylideneacetone)dipalladium(0); 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazolium tetrafluoroborate; lithium tert-butoxide / toluene / 4 h / 110 °C / Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → C23H27BBrOP (1429416-09-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; diisopropylamine / dichloromethane / Reflux 2.1: 1,4-diaza-bicyclo[2.2.2]octane 2.3: 0 °C View Scheme
Multi-step reaction with 2 steps 1.1: diisopropylamine; N-Bromosuccinimide / dichloromethane / 16 h / Inert atmosphere; Reflux 2.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 2.2: 2.67 h / 0 - 20 °C / Inert atmosphere 2.3: 1.17 h / 0 - 20 °C / Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → 2-boranatodiphenylphosphanyl-6-tert-pentylphenol (1429416-13-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; diisopropylamine / dichloromethane / Reflux 2.1: 1,4-diaza-bicyclo[2.2.2]octane 2.3: 0 °C 3.1: n-butyllithium / tetrahydrofuran / 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: diisopropylamine; N-Bromosuccinimide / dichloromethane / 16 h / Inert atmosphere; Reflux 2.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 2.2: 2.67 h / 0 - 20 °C / Inert atmosphere 2.3: 1.17 h / 0 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → (2R,3R,4aR,9aR)-7-(2-(diphenylphosphino)-6-tert-pentylphenoxy)-2,3-dimethoxy-2,3-dimethyl-5,5,9,9-tetraphenylhexahydro[1,4]dioxino[2,3-e][1,3,2]dioxaphosphepine

Conditions

Yield

Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; diisopropylamine / dichloromethane / Reflux 2.1: 1,4-diaza-bicyclo[2.2.2]octane 2.3: 0 °C 3.1: n-butyllithium / tetrahydrofuran / 0 °C 4.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 0.17 h / 20 °C / Inert atmosphere; Schlenk technique 4.2: 0 - 20 °C / Inert atmosphere; Schlenk technique 4.3: 0 - 20 °C / Inert atmosphere; Schlenk technique View Scheme

tert-amylphenol (3279-27-4) → (3aR,8aR)-6-(2-(diphenylphosphanyl)-6-(tert-pentyl)phenoxy)-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine (1429416-17-0)

Conditions

Yield

Multi-step reaction with 4 steps 1.1: diisopropylamine; N-Bromosuccinimide / dichloromethane / 16 h / Inert atmosphere; Reflux 2.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 2.2: 2.67 h / 0 - 20 °C / Inert atmosphere 2.3: 1.17 h / 0 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 2.5 h / 0 °C / Inert atmosphere 4.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 0.17 h / 20 °C / Schlenk technique; Inert atmosphere 4.2: 4 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 4.3: 21 h / 0 - 20 °C / Schlenk technique; Inert atmosphere View Scheme

tert-amylphenol (3279-27-4) → C18H29BO3 + C18H29BO3

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.67 h / 20 °C / Schlenk technique; Sealed tube 1.2: 3 h / Schlenk technique; Sealed tube 2.1: [(1,5-cyclooctadiene)(OH)iridium(I)]2; 2,2'-bis-[bis-(3,5-dimethyl-phenyl)-phosphanyl]-biphenyl / tert-butyl methyl ether / 20 h / 85 °C / Glovebox; Inert atmosphere; Sealed tube View Scheme

Upstream product

• 513-35-9 2-methyl-but-2-ene 
• 108-95-2 phenol 
• 594-36-5 2-methyl-2-butylchloride 
• 563-46-2 2-Methyl-1-butene 
• 80-46-6 4-t-amylphenol 
• 75-85-4 tert-Amyl alcohol 

Downstream Products

• 122269-08-3 2,4-dichloro-6-tert-pentyl-phenol 
• 87014-94-6 3.5-dinitro-2-hydroxy-1-tert-pentyl-benzene 
• 80-46-6 4-t-amylphenol 
• 1429416-17-0 (3aR,8aR)-6-(2-(diphenylphosphanyl)-6-(tert-pentyl)phenoxy)-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 
• 1429416-13-6 2-boranatodiphenylphosphanyl-6-tert-pentylphenol 
• 1429416-09-0 C₂₃H₂₇BBrOP 
• 1334501-77-7 2-(tert-Pentyl)-6-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1334501-86-8 2-(tert-pentyl)-6-(trimethylsilyl)phenol 
• 1334501-85-7 (2-bromo-6-(tert-pentyl)phenoxy)trimethylsilane 
• 5441-54-3 2-tert-Pentylcyclohexanon 
• 91242-72-7 cis-1-tert.-Pentyl-cyclohexanol-⁽²⁾ 

Relevant academic research and scientific papers

Zirconia-modified superacid UDCaT-5: An efficient and versatile catalyst for alkylation reactions under solvent-free conditions

UDCaT-5, a modified version of zirconia, efficiently catalyzes alkylation of phenols with alcohols under environmentally safe, heterogeneous reaction conditions with high selectivity and in excellent yields. The high content present in UDCaT-5 with preservation of tetragonal phase of zirconia was responsible for the superactivity. Several phenolic compounds carrying either electron-sulfer releasing or electron-withdrawing substituents in the ortho, meta, and para positions afforded high yields of the products. Copyright Taylor & Francis Group, LLC.

EQULIBRATION OF TERT-ALKYLPHENOLS (THERMODYNAMIC ANALYSIS OF THE ALKYLATION OF PHENOLS USING BRANCHED-CHAIN OLEFINS).

The authors describe the results of a study to evaluate the thermodynamic properties of t-Alk PHI ; these results; combined with earlier results, have enabled the authors to complete a thermodynamic analysis of the process for preparing tertiary alkylphenols.