4130-42-1

Basic information

• Product Name: 2,6-Ditert-butyl-4-ethylphenol
• Synonyms: ANTIOXIDANT BHEB;BHEB;2,6-bis(1,1-dimethylethyl)-4-ethylphenol;2,6-DI-TERT-BUTYL-1-HYDROXY-4-ETHYLBENZENE;2,6-DITERTIARY BUTYL-4-ETHYL PHENOL;2,6-DI-TERT-BUTYL-4-ETHYLPHENOL;TIMTEC-BB SBB008324;1-Hydroxy-4-ethyl-2,6-di-tert-butylbenzene
• CAS NO: 4130-42-1
• Molecular Formula: C₁₆H₂₆O
• Molecular Weight: 234.38
• EINECS: 223-945-2
• Product Categories: Aromatic Phenols;Organics
• Mol File: 4130-42-1.mol
• Article Data: 31

Chemical Properties

• Melting Point: >44°C
• Boiling Point: 272°C
• Flash Point: 105°C
• Appearance: /
• Density: 0.9260 (estimate)
• Vapor Pressure: 0.00375mmHg at 25°C
• Refractive Index: 1.5041 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.83±0.40(Predicted)
• BRN: 1875693
• CAS DataBase Reference: 2,6-Ditert-butyl-4-ethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Ditert-butyl-4-ethylphenol(4130-42-1)
• EPA Substance Registry System: 2,6-Ditert-butyl-4-ethylphenol(4130-42-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3077
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 4130-42-1(Hazardous Substances Data)

Usage

Uses

2,?6-?Di-?tert-?butyl-?4-?ethylphenol is used as a catalyst for the synthesis of aromatic carboxamides.

Purification Methods

Crystallise the phenol from aqueous EtOH or n-hexane. [Beilstein 6 IV 3529.]

InChI:InChI=1/C16H26O/c1-8-11-9-12(15(2,3)4)14(17)13(10-11)16(5,6)7/h9-10,17H,8H2,1-7H3

Synthetic route

ethanol (64-17-5) + 2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1)

Conditions	Yield
With potassium hydroxide; Pd/C; zinc(II) oxide at 200℃; for 15h;	76%

2,6-Di-tert-butyl-4-(1-hydroxyethyl)phenol (14681-20-0) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran; chlorobenzene for 1h; Heating;	70%

5,7-di-t-butylspiro[2.5]octa-4,7-dien-6-one (4309-85-7) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 1,4-bis-(3,5-di-tert-butyl-4-oxyphenyl)butane (42154-03-0)

Conditions	Yield
In N,N-dimethyl-formamide for 0.616667h; electrolysis, n-Bu4NClO4;	A 43% B 28%

2,6-di-tert-butylphenol (128-39-2) + paracetaldehyde (123-63-7) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 1,3-bis(3,5-di-tert-butyl-4-hydroxyphenyl)butane (718624-10-3) + 2,4-di-tert-Butylphenol (96-76-4) + 3-(3,5-di-tert-butyl-4-hydroxyphenyl)butan-1-ol (100669-72-5)

Conditions	Yield
With potassium hydroxide In ethanol at 230℃; for 0.333333h;	A n/a B 8% C 2% D 11.3%

2,6-di-tert-butylphenol (128-39-2) + acetaldehyde (75-07-0) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1)

Conditions	Yield
With sodium hydroxide; ethanol at 225℃;

4-Ethylphenol (123-07-9) + isobutene (115-11-7) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 6-di-t-butyl-4-ethylphenol (96-70-8)

Conditions	Yield
With sulfuric acid
With sulfuric acid at 70℃;

2,6-di-tert-butylphenol (128-39-2) + ethyl iodide (75-03-6) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 1,3-di-tert-butyl-2-ethoxybenzene (55704-26-2) + 2,6-Di-tert-butyl-4-aethyl-phenetol (94259-11-7) + 2,6-Di-tert.-butyl-4,4-diethyl-cyclohexadien-(2,5)-on-(1) (21565-57-1)

Conditions	Yield
(i) KOtBu, tBuOH, (ii) NaH, PE; Multistep reaction. Further byproducts given;

2,6-Di-tert-butyl-4-(1-hydroxyethyl)phenol (14681-20-0) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone (14035-33-7)

Conditions	Yield
aluminum oxide under 5 Torr; Heating; Yield given. Yields of byproduct given;

4-Aethyl-2,6-di-tert-butyl-phenoxyl-Radikal (13325-48-9) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-ethylidenecyclohexa-2,5-en-1-one (6738-27-8)

Conditions	Yield
Rate constant; Thermodynamic data; rate constant of the disproportionation;

4-ethyl-2,6-di-tert-butyl-4-hydroxy-2,5-cyclohexadienone (56207-20-6) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-Di-tert-butyl-4-ethyl-4-hydroxy-cyclohexanone + (4R,6S)-2,6-Di-tert-butyl-4-ethyl-4-hydroxy-cyclohex-2-enone

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate In methanol at 30℃; for 48h; Yield given. Yields of byproduct given;

4-Ethylphenol (123-07-9) + sulfuric acid (7664-93-9) + isobutene (115-11-7) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 6-di-t-butyl-4-ethylphenol (96-70-8)

2,6-di-tert-butylphenol (128-39-2) + crotonaldehyde (123-73-9) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 1,3-bis(3,5-di-tert-butyl-4-hydroxyphenyl)butane (718624-10-3) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 1,1-bis(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (19072-87-8) + 3-(3,5-di-tert-butyl-4-hydroxyphenyl)butan-1-ol (100669-72-5)

Conditions	Yield
With potassium hydroxide In ethanol at 230℃; for 0.5h;	A 10 g B n/a C n/a D n/a E 3 g

2,6-di-tert-butylphenol (128-39-2) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-propyllphenol (4973-24-4) + 1,2-bis(2,6-di-tert-butyl-4-hydroxyphenyl)ethane (96469-23-7) + 1,4-bis(2,6-di-tert-butyl-4-hydroxyphenyl)butane + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 2,6-di-tert-butyl-4-isopropylphenol (5427-03-2) + 2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol (3673-68-5) + ethylene glycol 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-ethyl ether (39169-63-6) + 6-di-t-butyl-4-ethylphenol (96-70-8) + 4-butyl-2,6-di-tert-butylphenol (5530-30-3)

Conditions	Yield
With sodium hydroxide at 220℃; for 5h;

...Expand

4-methoxy-phenol (150-76-5) + ethylphenol + propylphenol + butylphenol + pentylphenol → 4-Ethylphenol (123-07-9) + 2,6-di-tert-butylphenol (128-39-2) + 3-ethylphenol (620-17-7) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 3,5-diisopropylphenol (26886-05-5) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,4-di-tert-Butylphenol (96-76-4) + 3,5-diethylphenol (1197-34-8) + 2,4-diethylphenol (936-89-0) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 2,5-di-(sec-butyl)phenol (54932-77-3)

Conditions	Yield
With molybdenum(VI) oxide In ethanol at 280℃; for 4h; Inert atmosphere;

...Expand

2-Ethoxyphenol (94-71-3) + ethylphenol + propylphenol + butylphenol + pentylphenol + methylphenol → mono-tert-butyl-m-cresol + 4-Ethylphenol (123-07-9) + 2,6-di-tert-butylphenol (128-39-2) + 3-ethylphenol (620-17-7) + 2,4-diisopropylphenol (2934-05-6) + Durohydroquinone (527-18-4) + 2,6-diisopropylphenol (2078-54-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 3,5-Di-tert-butylphenol (1138-52-9) + 3,5-diethylphenol (1197-34-8) + 2,5-di-tert-butylphenol (5875-45-6) + 2,5-Diisopropylphenol (35946-91-9) + 2,5-diethyl phenol (876-20-0)

Conditions	Yield
With molybdenum(VI) oxide In ethanol at 280℃; for 4h; Inert atmosphere;

...Expand

benzene-1,2-diol (120-80-9) + ethylphenol + propylphenol + butylphenol → 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 3,5-diethylphenol (1197-34-8) + 2,5-di-tert-butylphenol (5875-45-6) + 2,5-diethyl phenol (876-20-0) + 2,5-di-(sec-butyl)phenol (54932-77-3)

Conditions	Yield
With molybdenum(VI) oxide In ethanol at 280℃; for 4h; Inert atmosphere;

...Expand

2-methoxy-phenol (90-05-1) + ethylphenol + propylphenol + butylphenol + pentylphenol → o-Hydroxyethylbenzene (90-00-6) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,4-di-tert-Butylphenol (96-76-4) + 3,5-diethylphenol (1197-34-8) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 2,5-di-(sec-butyl)phenol (54932-77-3)

Conditions	Yield
With molybdenum(VI) oxide In ethanol at 280℃; for 4h; Catalytic behavior; Temperature; Solvent; Time; Reagent/catalyst; Inert atmosphere;

...Expand

2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: water; methanol / 3 h / 90 °C 2: palladium; hydrogen / 4 h / 140 °C View Scheme

N,N-dimethyl-2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethylamine (83698-88-8) → 2,6-di-tert-butyl-4-ethylphenol (4130-42-1)

Conditions	Yield
With hydrogen; palladium at 140℃; for 4h;	225.37 g

ethanol (64-17-5) + 2-methoxy-phenol (90-05-1) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With ortho-tungstic acid at 300℃; for 6h; Autoclave;

...Expand

ethanol (64-17-5) + 2-methoxy-phenol (90-05-1) → 2-Ethoxyphenol (94-71-3) + 3,5-Di-tert-butylcatechol (1020-31-1) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With tungsten(VI) oxide at 300℃; for 6h; Reagent/catalyst; Autoclave;

...Expand

ethanol (64-17-5) + benzene-1,2-diol (120-80-9) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With ortho-tungstic acid at 300℃; for 6h; Autoclave;

...Expand

2-Ethoxyphenol (94-71-3) + ethanol (64-17-5) → 3,5-Di-tert-butylcatechol (1020-31-1) + 2,6-di-tert-butylphenol (128-39-2) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,4,6-triisopropylphenol (2934-07-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-di-tert-butyl-4-methoxymethylene-phenol (87-97-8) + 3,5-Di-tert-butylphenol (1138-52-9) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-(2',5'-dimethoxyphenyl)propionaldehyde (52417-48-8) + 2,6-di-tert-butyl-4-sec-butylphenol (17540-75-9) + 1,2-diethoxybenzene (2050-46-6) + 1,4-dimethoxy-2-tert-butylbenzene (21112-37-8) + 1-ethoxy-4-methoxybenzene (5076-72-2) + 2,5-di(tert-amyl)-1,4-hydroquinone (79-74-3) + 2,4-di-tert-amylphenol (120-95-6) + 2,5-diethyl phenol (876-20-0) + 4-ethoxy-3-methoxytoluene (33963-27-8) + 1,2-dimethoxy-4-butylbenzene (59056-76-7) + 1,2-diethoxy-4-ethyl-benzene (131358-04-8) + 3,5-di-t-butyl-4-hydroxybenzaldehyde (1620-98-0)

Conditions	Yield
With ortho-tungstic acid at 300℃; for 6h; Autoclave;

...Expand

ethanol (64-17-5) + 2-methoxy-phenol (90-05-1) → o-Hydroxyethylbenzene (90-00-6) + 2,6-di-tert-butylphenol (128-39-2) + 3-ethylphenol (620-17-7) + 2,4-diisopropylphenol (2934-05-6) + 2,6-diisopropylphenol (2078-54-8) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + 1,4-diethylbenzene (105-05-5) + 3,5-diethylphenol (1197-34-8) + 2,5-di-tert-butylphenol (5875-45-6) + 1,3,5-triethylbenzene (102-25-0) + 4-Ethylguaiacol (2785-89-9) + 2,5-diethyl phenol (876-20-0) + 2,4-diisopropyl-5-methylphenol (40625-96-5) + 1-(2,4,5-triethylphenyl)ethanone (2715-54-0) + 1-ethyl-3-tert-butyl-5-methyl-benzene (6630-01-9) + methoxybenzene (100-66-3) + phenol (108-95-2)

Conditions	Yield
With perrhenic acid anhydride at 320℃; for 6h; Inert atmosphere; Sealed tube;

...Expand

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 4-ethyl-2,6-di-tert-butyl-4-hydroxy-2,5-cyclohexadienone (56207-20-6)

Conditions	Yield
With cesium hydroxide; oxygen; triethyl phosphite In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h;	96%
With perchloric acid; water; lead dioxide In acetone for 0.133333h;	83%
With potassium tert-butylate; oxygen

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 2,6-di-tert-butyl-4-ethyl-4-hydroperoxycyclohexa-2,5-dienone (87013-27-2)

Conditions	Yield
With 2,8-dibromo-5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-5H-dipyrrolo[1,2-c:2′,1′-f ][1,3,2]diazaborinin-4-ium-5-uide; oxygen In 1,4-dioxane for 6h; Irradiation;	96%
With potassium hydroxide; oxygen In ethanol; water	70%
With potassium hydroxide; oxygen In ethanol at 0 - 5℃; for 14h;

ethyl 2-bromoisobutyrate (600-00-0) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → ethyl 2-(3,5-di-tert-butyl-1-ethyl-4-oxocyclohexa-2,5-dien-1-yl)-2-methylpropanoate

Conditions	Yield
With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 1h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;	96%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + C16H19BrO3 → 4-(3-hydroxy-3-methylbut-1-yn-1-yl)benzyl 2-(3,5-di-tert-butyl-1-ethyl-4-oxocyclohexa-2,5-dien-1-yl)-2-methylpropanoate

Conditions	Yield
With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 1h; Inert atmosphere;	91%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → (Z)-1-[4-(2,6-di-tert-butyl-4-ethylcyclohexadienonyl)]-diazen-1-ium-1,2-diolinic acid

Conditions	Yield
With nitrogen(II) oxide; sodium In methanol at 20℃; under 1810.07 Torr; for 24h; Addition;	88%

methanol (67-56-1) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 2,6-di-tert-butyl-4-methoxy-4-ethylcyclohexa-2,5-dienone

Conditions	Yield
With perchloric acid; lead dioxide for 0.133333h;	88%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + C13H16Br2O2 → 4-bromobenzyl 2-(3,5-di-tert-butyl-1-ethyl-4-oxocyclohexa-2,5-dien-1-yl)-2-ethylbutanoate

Conditions	Yield
With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 20h; Inert atmosphere;	88%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + C11H19Br3O2 → 2-bromoallyl 2-(3,5-di-tert-butyl-1-ethyl-4-oxocyclohexa-2,5-dien-1-yl)-2-propylpentanoate

Conditions	Yield
With copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,4'-di-tert-butyl-2,2'-bipyridine In toluene at 20℃; for 20h; Inert atmosphere;	80%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 4-Ethylphenol (123-07-9) + 6-di-t-butyl-4-ethylphenol (96-70-8)

Conditions	Yield
at 270℃; for 24h; Product distribution; reaction time 8 h;	A 2 % Chromat. B 78%
at 270℃; for 24h;	A 2 % Chromat. B 78%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 5,7-di-tert-butyl-2-methyl-1-oxa-spiro[2.5]octa-4,7-dien-6-one (65076-91-7)

Conditions	Yield
With sodium hypochlorite pentahydrate; tetra-(n-butyl)ammonium iodide In ethyl acetate at 25℃; for 0.5h; Green chemistry; chemoselective reaction;	77%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + methoxybenzene (100-66-3) → 2,6-di-tert-butyl-4-(4-methoxyphenyl)-4-ethylcyclohexa-2,5-dien-1-one (1127943-54-7)

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In 1,1,1,3',3',3'-hexafluoro-propanol at 0℃; for 0.0388889h; oxidative Friedel Crafts reaction; regioselective reaction;	70%
With bis-[(trifluoroacetoxy)iodo]benzene In 1,1,1,3',3',3'-hexafluoro-propanol oxidative Friedel-Crafts reaction;	70%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + sodium benzenesulfonate (873-55-2) → 2,6-di-tert-butyl-4-(1-(phenylsulfonyl)ethyl)phenol (60131-46-6)

Conditions	Yield
With tert.-butylhydroperoxide; iodine In chloroform at 20℃; for 12h; regioselective reaction;	68%

tert.-butylhydroperoxide (75-91-2) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + sodium 4-methylbenzenesulfinate (824-79-3) → 2,6-di-tert-butyl-4-(tert-butylperoxy)-4-(1-tosylethyl)cyclohexa-2,5-dien-1-one

Conditions	Yield
With iodine In chloroform at 20℃; for 12h; regioselective reaction;	64%

4-n-chlorophenylacetylene (873-73-4) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → C24H30ClN3O

Conditions	Yield
With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	63%

N,N'-(3,3'-bis(propyl)amine)bis(salicylideneiminato)cobalt(II) (15306-22-6) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → C6H2(C(CH3)3)2CH2CH3OOOCo(NCHC6H4O)2(CH2)3NH(CH2)3*H2O

Conditions	Yield
With O2 In dichloromethane mixt. was stirred with O2 bubbling at 0°C for 2-4 h; soln. was concd. in vac. below 20°C, light petroleum was added, soln. was allowed to stand in a refrigerator overnight, crystals were collected, washed with a mixt. of light petroleum and CH2Cl2, dried in vac.; elem. anal.;	62%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + phenylacetylene (536-74-3) → C24H31N3O

Conditions	Yield
With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	61%

tert.-butylhydroperoxide (75-91-2) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + sodium 4-fluorobenzenesulfinate (824-80-6) → 2,6-di-tert-butyl-4-(tert-butylperoxy)-4-(1-((4-fluorophenyl)sulfonyl)ethyl)cyclohexa-2,5-dien-1-one

Conditions	Yield
With iodine In chloroform at 20℃; for 12h; regioselective reaction;	58%

tert.-butylhydroperoxide (75-91-2) + 2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + sodium p-chlorobenzenesulphinate (14752-66-0) → 2,6-di-tert-butyl-4-(tert-butylperoxy)-4-(1-((4-chlorophenyl)sulfonyl)ethyl)cyclohexa-2,5-dien-1-one

Conditions	Yield
With iodine In chloroform at 20℃; for 12h; regioselective reaction;	56%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + sodium thiophene-2-sulphinate (38945-01-6) → 2,6-di-tert-butyl-4-(1-(thiophen-2-ylsulfonyl)ethyl)phenol

Conditions	Yield
With tert.-butylhydroperoxide; iodine In chloroform at 20℃; for 12h; regioselective reaction;	47%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one (14387-13-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(ll) bromide In toluene at 20℃; for 1h; Inert atmosphere;	18%

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 2,6-di-tert-butyl-4-ethylidenecyclohexa-2,5-en-1-one (6738-27-8)

Conditions	Yield
With potassium hexacyanoferrate(III); benzene
With potassium hydroxide; potassium hexacyanoferrate(III)
With sodium persulfate; sodium hexacyanoferrate(II) decahydrate; sodium hydroxide In hexane; water for 4h; Inert atmosphere;
With sodium peroxydisulfate; sodium hexacyanoferrate(II) decahydrate; sodium hydroxide In hexane; water for 4h; Inert atmosphere;
With potassium hydroxide; potassium hexacyanoferrate(III) In water at 23℃; for 1h; Inert atmosphere;

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone (14035-33-7)

Conditions	Yield
With Isopropylbenzene; Cumene hydroperoxide; cobalt(II) o-phthalate at 80 - 100℃; Behandeln mit Luft;

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) → 2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol (3673-68-5) + 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone (14035-33-7)

Conditions	Yield
With Isopropylbenzene; air; Cumene hydroperoxide; cobalt(II) o-phthalate at 80 - 100℃;

2,6-di-tert-butyl-4-ethylphenol (4130-42-1) + benzoyl chloride (98-88-4) → benzoic acid-(4-ethyl-2,6-di-tert-butyl-phenyl ester)

Upstream product

• 128-39-2 2,6-di-tert-butylphenol 
• 75-07-0 acetaldehyde 
• 123-07-9 4-Ethylphenol 
• 115-11-7 isobutene 
• 14681-20-0 2,6-Di-tert-butyl-4-(1-hydroxyethyl)phenol 
• 56207-20-6 4-ethyl-2,6-di-tert-butyl-4-hydroxy-2,5-cyclohexadienone 
• 7664-93-9 sulfuric acid 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 98324-84-6 1-(2-(methylthio)phenyl)-3-phenylprop-2-yn-1-one 
• 90-05-1 2-methoxy-phenol 
• 120-80-9 benzene-1,2-diol 
• 94-71-3 2-Ethoxyphenol 
• 150-76-5 4-methoxy-phenol 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 

Downstream Products

• 94259-11-7 2,6-Di-tert-butyl-4-aethyl-phenetol 
• 21565-57-1 2,6-Di-tert.-butyl-4,4-diethyl-cyclohexadien-(2,5)-on-⁽¹⁾ 
• 123-07-9 4-Ethylphenol 
• 96-70-8 6-di-t-butyl-4-ethylphenol 
• 87013-27-2 2,6-di-tert-butyl-4-ethyl-4-hydroperoxycyclohexa-2,5-dienone 
• 115-11-7 isobutene 
• 198976-23-7 2,6-Di-tert-butyl-4-chloro-4-ethyl-cyclohexa-2,5-dienone 
• 3673-68-5 2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol 
• 14035-33-7 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone 
• 1127943-54-7 2,6-di-tert-butyl-4-(4-methoxyphenyl)-4-ethylcyclohexa-2,5-dien-1-one 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 14387-13-4 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-methyl-2,5-cyclohexadiene-1-one 

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