1879-09-0

Basic information

• Product Name: 2-(tert-Butyl)-4,6-dimethylphenol
• Synonyms: Butyldimethylphenol;TERT-BUTYL-2,4-DIMETHYLPHENOL;2-(tert-Butyl)-4,6-dimethylphenol, tech;6-TERT-BUTYL-2,4-XYLENOL 98%;2-TERTBUTYL-4-CRESOL 2409-55-4;Topnol A;Antioxidant 6BX;Antioxidant AO 30
• CAS NO: 1879-09-0
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.27
• EINECS: 217-533-1
• Product Categories: Industrial/Fine Chemicals;Pyridines
• Mol File: 1879-09-0.mol
• Article Data: 29

Chemical Properties

• Melting Point: 22 °C
• Boiling Point: 249°C
• Flash Point: 112°C
• Appearance: yellow liquid
• Density: 0,917 g/cm3
• Vapor Pressure: 4.2Pa at 25℃
• Refractive Index: 1.5183
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Insoluble in water
• PKA: 12.00±0.23(Predicted)
• Water Solubility: 120mg/L at 20℃
• CAS DataBase Reference: 2-(tert-Butyl)-4,6-dimethylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(tert-Butyl)-4,6-dimethylphenol(1879-09-0)
• EPA Substance Registry System: 2-(tert-Butyl)-4,6-dimethylphenol(1879-09-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2927
• RTECS: ZE6825000
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 1879-09-0(Hazardous Substances Data)

Usage

Uses

6-tert-Butyl-2,4-xylenol is an antioxidant found used in rocket and jet fuels.

General Description

A yellow liquid with a phenolic odor. Insoluble in water and about the same density as water. Exposure to skin, eyes or mucous membranes may cause severe burns.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Phenols, such as 2-(tert-Butyl)-4,6-dimethylphenol, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

InChI:InChI=1/C15H16Cl3N3O2.C15H24O/c1-2-4-20(15(22)21-5-3-19-10-21)6-7-23-14-12(17)8-11(16)9-13(14)18;1-10-8-11(14(2,3)4)13(16)12(9-10)15(5,6)7/h3,5,8-10H,2,4,6-7H2,1H3;8-9,16H,1-7H3

Synthetic route

2,4-Xylenol (105-67-9) + isobutene (115-11-7) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
Stage #1: 2,4-Xylenol With zinc Heating; Large scale; Stage #2: isobutene at 70℃; Large scale;	96.1%
With acidic ion exchanger
With sulfuric acid at 70℃;
With toluene-4-sulfonic acid In toluene	253 g (86.6%)

methanol (67-56-1) + 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane (119-47-1) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
With zinc(II) oxide; sodium hydroxide at 250℃; for 8h;	94%

methanol (67-56-1) + 2-tert-Butyl-6-methylphenol (2219-82-1) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
With zinc(II) oxide; sodium hydroxide at 210 - 220℃; for 8h;	84%

2-(allyloxy)-1-(tert-butyl)-3,5-dimethylbenzene → 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2-allyl-4,6-dimethylphenol (19182-94-6)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 220℃; for 0.333333h; Claisen Rearrangement; Microwave irradiation; Inert atmosphere;	A 23% B 42%

2,4-Xylenol (105-67-9) + tert-butyl alcohol (75-65-0) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 3h; Heating;	A 83 g B 25.8%
With toluene-4-sulfonic acid In benzene for 3h; Heating;	A 83 mg B 25.8%

2,5-dimethyl-4-(1,1-dimethylethyl)-phenol (17696-37-6) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
With sodium hydroxide

2,4-Xylenol (105-67-9) + tert-butyl alcohol (75-65-0) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
With phosphoric acid at 70 - 105℃;
With phosphoric acid; phosphorus pentoxide

phosphoric acid (86119-84-8, 7664-38-2) + 2,4-Xylenol (105-67-9) + tert-butyl alcohol (75-65-0) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
at 70 - 105℃;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4,4'-Methylenebis(2,6-di-tert-butylphenol) (118-82-1) + 3,5-di-tert-butyl-4-hydroxy benzyl chloride (955-01-1) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
palladium on activated charcoal In toluene

5,11,17,23-tetratert-butyl-4,12,16,24-tetrahydroxycalix[4]arene ethanol complex → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 °C 2: zinc(II) oxide; sodium hydroxide / 8 h / 250 °C View Scheme

5,11,17,23-tetratert-butyl-4,12,16,24-tetrahydroxycalix[4]arene → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: Reflux 2: 100 °C 3: zinc(II) oxide; sodium hydroxide / 8 h / 250 °C View Scheme

2-tert-Butylphenol (88-18-6) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Fe2O3-MnO-V2O5 / 290 °C / Gas phase 2: zinc(II) oxide; sodium hydroxide / 8 h / 210 - 220 °C View Scheme
Multi-step reaction with 2 steps 1: Fe2O3-MnO-V2O5 / 325 °C / Gas phase 2: zinc(II) oxide; sodium hydroxide / 8 h / 210 - 220 °C View Scheme
Multi-step reaction with 2 steps 1: zinc(II) oxide; sodium hydroxide / 15 h / 250 °C / Autoclave 2: zinc(II) oxide; sodium hydroxide / 8 h / 210 - 220 °C View Scheme

6-tert-butyl-2-(2'-methoxy-3'-tert-butyl-5'-methylbenzyl)-4-methylphenol (27996-19-6) → 2-tert-Butyl-6-methylphenol (2219-82-1) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane (119-47-1)

Conditions	Yield
With zinc(II) oxide; sodium hydroxide In methanol at 220℃; for 4h;

6-tert-butyl-2-(2'-methoxy-3'-tert-butyl-5'-methylbenzyl)-4-methylphenol (27996-19-6) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) oxide; sodium hydroxide / methanol / 4 h / 220 °C 2: zinc(II) oxide; sodium hydroxide / 8 h / 210 - 220 °C View Scheme
Multi-step reaction with 2 steps 1: zinc(II) oxide; sodium hydroxide / methanol / 4 h / 220 °C 2: zinc(II) oxide; sodium hydroxide / 8 h / 250 °C View Scheme

2-(N,N-dimethylaminomethyl)-6-tert-butylphenol (64325-12-8) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium (4%) on activated charcoal; hydrogen / 11 h / 130 °C / 37503.8 Torr / Autoclave 2: zinc(II) oxide; sodium hydroxide / 8 h / 210 - 220 °C View Scheme

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

2,4-Xylenol (105-67-9) + isobutene (115-11-7) → 2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2,4-dimethyl-5-tert-butylphenol

Conditions	Yield
With toluene-4-sulfonic acid In water at 65℃; under 759.826 Torr; for 0.5h; Activation energy; Pressure; Concentration;

formaldehyd (50-00-0) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl chloride (23500-79-0)

Conditions	Yield
With hydrogenchloride; tetrabutylammomium bromide at 20℃; Reagent/catalyst;	97.2%
Stage #1: formaldehyd; 2,4-dimethyl-6-tert-butylphenol With hydrogenchloride In water at 37℃; for 2h; Stage #2: With phosphorus trichloride at 40℃; for 5h;

Togni's reagent II (887144-94-7) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2-(tert-butyl)-6-methyl-4-(2,2,2-trifluoroethyl)phenol

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide at 40℃; for 1h; Reagent/catalyst; Solvent; Schlenk technique;	93%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 3-tert-butyl-4-hydroxy-5-methylbenzaldehyde (10537-77-6)

Conditions	Yield
With copper diacetate; ethylene glycol at 65℃; for 12h; Green chemistry; regioselective reaction;	84%
With oxygen; cobalt(II) acetate; sodium hydroxide In water; ethylene glycol at 50℃; under 760.051 Torr; for 12h; Green chemistry; chemoselective reaction;	83%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + sodium benzenesulfonate (873-55-2) → 2-(tert-butyl)-6-methyl-4-((phenylsulfonyl)methyl)phenol

Conditions	Yield
With iodine; copper diacetate In acetonitrile at 20℃; for 12h; regioselective reaction;	83%

4-n-chlorophenylacetylene (873-73-4) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → C20H22ClN3O

Conditions	Yield
With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	79%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + phenylacetylene (536-74-3) → C20H23N3O

Conditions	Yield
With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	76%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 4-n-methylphenylacetylene (766-97-2) → C21H25N3O

Conditions	Yield
With potassium fluoride; sodium azide; silver carbonate In N,N-dimethyl-formamide at 50℃; for 6h;	73%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) → C12H18O2

Conditions	Yield
With cesium hydroxide; oxygen; triethyl phosphite In dimethyl sulfoxide at 25℃; under 760.051 Torr; for 12h;	71%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + p-tolyldiazonium tetrafluoroborate → 2-(tert-butyl)-6-methyl-4-(tosylmethyl)phenol

Conditions	Yield
With sodium metabisulfite; tris[2-phenylpyridinato-C2,N]iridium(III); sodium hydrogencarbonate In 1,2-dichloro-ethane at 20℃; Inert atmosphere; Irradiation;	70%

Dimethoxymethane (109-87-5) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 3-(bromomethyl)-6-tert-butyl-2,4-dimethylphenol (93982-04-8)

Conditions	Yield
With hydrogen bromide	68%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + propionyl chloride (79-03-8) → 2-tert-butyl-4,6-dimethylphenyl propionate

Conditions	Yield
Stage #1: 2,4-dimethyl-6-tert-butylphenol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	67%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 3-chloroprop-1-ene (107-05-1) → 2-(allyloxy)-1-(tert-butyl)-3,5-dimethylbenzene

Conditions	Yield
Stage #1: 2,4-dimethyl-6-tert-butylphenol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 3-chloroprop-1-ene In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	67%

Togni's reagent II (887144-94-7) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2-(tert-butyl)-6-methyl-4-(2,2,2-trifluoroethyl)phenol + 6-(tert-butyl)-2,4-dimethyl-3-(trifluoromethyl)phenol

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate In tert-butyl alcohol at 40℃; Reagent/catalyst; Solvent;	A 6% B 54%

Togni's reagent II (887144-94-7) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 6-(tert-butyl)-2,4-dimethyl-3-(trifluoromethyl)phenol

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate In tert-butyl alcohol at 40℃; Schlenk technique;	54%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + phenyldiazonium tetrafluoroborate → 2-(tert-butyl)-6-methyl-4-((phenylsulfonyl)methyl)phenol

Conditions	Yield
With sodium metabisulfite; tris[2-phenylpyridinato-C2,N]iridium(III); sodium hydrogencarbonate In 1,2-dichloro-ethane at 20℃; Inert atmosphere; Irradiation;	53%

ethanol (64-17-5) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 3-tert-butyl-4-hydroxy-5-methylbenzaldehyde (10537-77-6) + 2-t-butyl-4-(ethoxymethyl)-2-methylphenol (134778-32-8)

Conditions	Yield
With oxygen; copper dichloride; acetone oxime at 40℃; under 860.3 Torr; for 1.41667h;	A 5% B 49%
With oxygen; acetone oxime at 40℃; under 860.3 Torr; for 1.41667h; Yield given. Yields of byproduct given;

2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 3-tert-butyl-4-hydroxy-5-methylbenzaldehyde (10537-77-6) + 2-t-butyl-4-(ethoxymethyl)-2-methylphenol (134778-32-8)

Conditions	Yield
With oxygen; copper dichloride; acetone oxime In ethanol at 40℃; under 860.3 Torr; for 1.41667h;	A 5% B 49%
With oxygen; acetone oxime In ethanol at 40℃; under 860.3 Torr; for 1.41667h; Yield given. Yields of byproduct given;

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + 2,4,4,4-tetrafluoro-3,3-dihydroxy-1-phenylbutan-1-one → (S)-3-(3-(tert-butyl)-4-hydroxy-5-methylphenyl)-2-fluoro-1-phenylpropan-1-one

Conditions	Yield
Stage #1: 2,4-dimethyl-6-tert-butylphenol; 2,4,4,4-tetrafluoro-3,3-dihydroxy-1-phenylbutan-1-one With potassium dihydrogenphosphate; tetrabutylammonium perchlorate; C34H37N3O4 In 1,2-dichloro-ethane at 70℃; Inert atmosphere; Electrochemical reaction; Stage #2: With potassium hydrogencarbonate In 1,2-dichloro-ethane at 70℃; for 3h; Inert atmosphere; enantioselective reaction;	49%

formaldehyd (50-00-0) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 3-(bromomethyl)-6-tert-butyl-2,4-dimethylphenol (93982-04-8)

Conditions	Yield
With hydrogen bromide; acetic acid at 45℃; Inert atmosphere;	41%

Togni's reagent II (887144-94-7) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2,2,6,6-tetramethyl-1-(trifluoromethoxy)piperidine (1335135-19-7) + 3,3'-di-tert-butyl-5,5'-dimethyl-bibenzyl-4,4'-diol

Conditions	Yield
With copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In N,N-dimethyl-formamide at 40℃; for 1h; Schlenk technique;	A 58 %Spectr. B 38%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + benzyl bromide (100-39-0) → 6-benzyl-2-(tert-butyl)-4,6-dimethylcyclohexa-2,4-dien-1-one (125211-83-8)

Conditions	Yield
Stage #1: 2,4-dimethyl-6-tert-butylphenol With n-butyllithium In hexane; toluene for 0.25h; Inert atmosphere; Stage #2: benzyl bromide In toluene at 80℃; Reagent/catalyst; Temperature; Inert atmosphere;	35%

tert.-butylhydroperoxide (75-91-2) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2-tert-butyl-6-methyl-1,4-benzoquinone (25543-57-1) + 2-t-butyl-4-t-butylperoxy-4,6-dimethyl-2,5-cyclohexadien-1-one (136613-00-8)

Conditions	Yield
phosphomolybdic acid hydrate In acetic acid at 30℃; for 3h;	A 11.5% B 33.5%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2-tert-butyl-6-methyl-1,4-benzoquinone (25543-57-1) + 2-t-butyl-4-t-butylperoxy-4,6-dimethyl-2,5-cyclohexadien-1-one (136613-00-8)

Conditions	Yield
With tert.-butylhydroperoxide; phosphomolybdic acid hydrate In acetic acid at 30℃; for 3h;	A 11.5% B 33.5%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) + acetonitrile (75-05-8) → N-tert-butylacetamide (762-84-5) + 4-tert-butyl-2,5,7-trimethylbenzoxazole (139656-52-3) + 2,4-Xylenol (105-67-9) + isobutene (115-11-7)

Conditions	Yield
With thianthrene cation radical perchlorate for 3h; Further byproducts given;	A 6.5% B 14% C 5.8% D 25%

tert.-butylhydroperoxide (75-91-2) + 2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 2-t-butyl-4-t-butylperoxy-4,6-dimethyl-2,5-cyclohexadien-1-one (136613-00-8) + 2,2'-di-tert-butyl-6,6'-dimethyl-4,4'-ethanediylidene-bis-cyclohexa-2,5-dienone (147120-00-1)

Conditions	Yield
With cobalt naphthenate; benzene

Upstream product

• 105-67-9 2,4-Xylenol 
• 75-65-0 tert-butyl alcohol 
• 67-56-1 methanol 
• 2219-82-1 2-tert-Butyl-6-methylphenol 
• 119-47-1 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane 
• 88-18-6 2-tert-Butylphenol 
• 27996-19-6 6-tert-butyl-2-(2'-methoxy-3'-tert-butyl-5'-methylbenzyl)-4-methylphenol 
• 64325-12-8 2-(N,N-dimethylaminomethyl)-6-tert-butylphenol 
• 115-11-7 isobutene 
• 94-71-3 2-Ethoxyphenol 
• 64-17-5 ethanol 
• 120-80-9 benzene-1,2-diol 
• 90-05-1 2-methoxy-phenol 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 

Downstream Products

• 136613-00-8 2-t-butyl-4-t-butylperoxy-4,6-dimethyl-2,5-cyclohexadien-1-one 
• 147120-00-1 2,2'-di-tert-butyl-6,6'-dimethyl-4,4'-ethanediylidene-bis-cyclohexa-2,5-dienone 
• 105-67-9 2,4-Xylenol 
• 10537-77-6 3-tert-butyl-4-hydroxy-5-methylbenzaldehyde 
• 134778-32-8 2-t-butyl-4-(ethoxymethyl)-2-methylphenol 
• 64833-91-6 6-t-Butyl-2,4-xylenylformat 
• 29808-60-4 2,4-Dimethyl-6-tert.-butylphenylcyanat 
• 125211-83-8 6-benzyl-2-(tert-butyl)-4,6-dimethylcyclohexa-2,4-dien-1-one 
• 93982-04-8 3-(bromomethyl)-6-tert-butyl-2,4-dimethylphenol 
• 23500-79-0 2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl chloride 
• 762-84-5 N-tert-butylacetamide 
• 139656-52-3 4-tert-butyl-2,5,7-trimethylbenzoxazole 
• 115-11-7 isobutene 
• 60301-94-2 Carbanilsaeure-<2-tert-butyl-4.6-dimethyl-phenylester> 

Relevant articles and documents

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Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

Phenol o-position alkylation method

The invention provides a phenol o-position alkylation method which comprises the following step: in the presence of a catalyst, a phenol substance and an alkylating agent react, wherein the catalyst is an aryl zinc salt generated from a reaction of zinc and a phenol compound; the alkylating agent is olefin; the phenol substance comprises polyphenol such as catechol and hydroquinone, and further comprises one to two alkyl groups, or halide based phenols; the alkyl group is straight-chain or branched paraffin with 1-10 carbons. By adopting the phenol o-position alkylation method, the preparation efficiency is greatly improved, and the conversion rate can be further increased. The invention further provides a method for preparing 2,6-di-tert-butyl-4-methylphenol, and a reaction kettle for preparation.