489-01-0

Basic information

• Product Name: 2,6-DI-TERT-BUTYL-4-METHOXYPHENOL
• Synonyms: 2,6-Bis(tert-butyl)-4-methoxyphenol;DTBHA;2,6-Di-tert-butyl-4-methoxyphenol,97%;2,6-Di-tert-butyl-4-methoxyphenol,3,5-Di-tert-butyl-4-hydroxyanisole;2,6-Di-tert-butyl-4-Methoxyphenol, 97% 100GR;2,6-Di-tert-butyl-4-Methoxyphenol, 97% 25GR;[Oxidation inhibitor];2,6-Di-tert-butyl-4-Methoxyphenol
• CAS NO: 489-01-0
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.35
• EINECS: 207-693-0
• Product Categories: Aromatic Ethers;Heterocyclic Compounds
• Mol File: 489-01-0.mol
• Article Data: 49

Chemical Properties

• Melting Point: 102-106 °C(lit.)
• Boiling Point: 135-140°C 10mm
• Flash Point: 135-140°C/10mm
• Appearance: Clear/Liquid
• Density: 0.9845 (rough estimate)
• Vapor Pressure: 0.000757mmHg at 25°C
• Refractive Index: 1.5542 (estimate)
• Solubility: soluble in Methanol
• PKA: 13.04±0.40(Predicted)
• BRN: 2052290
• CAS DataBase Reference: 2,6-DI-TERT-BUTYL-4-METHOXYPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DI-TERT-BUTYL-4-METHOXYPHENOL(489-01-0)
• EPA Substance Registry System: 2,6-DI-TERT-BUTYL-4-METHOXYPHENOL(489-01-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: SJ7785668
• Hazardous Substances Data: 489-01-0(Hazardous Substances Data)

Usage

Description

2,6-Di-tert-butyl-4-methoxyphenol is a phenolic antioxidant characterized by its white to beige crystalline powder form. It is known for its ability to protect cosmetics, drugs, and foods from oxidative degradation due to its antioxidant properties. Additionally, it participates in In(trifluoromethanesulfonate)3-catalyzed tandem reactions with various nucleophiles, showcasing its versatility in chemical applications.

Uses

Used in Cosmetics Industry:
2,6-Di-tert-butyl-4-methoxyphenol is used as an antioxidant for the cosmetic industry to protect products from oxidative degradation, ensuring their stability, and prolonging their shelf life. This helps maintain the quality, appearance, and effectiveness of cosmetics over time.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,6-Di-tert-butyl-4-methoxyphenol serves as an antioxidant to protect drugs from oxidation, which can lead to the degradation of active ingredients and a reduction in their therapeutic effects. By incorporating this antioxidant, the pharmaceutical industry can enhance the stability and efficacy of medications.
Used in Food Industry:
2,6-Di-tert-butyl-4-methoxyphenol is used as an additive in the food industry to prevent oxidative spoilage, which can cause rancidity and off-flavors in various food products. Its antioxidant properties help maintain the freshness, taste, and nutritional value of the food items, thus extending their shelf life and ensuring consumer safety.
Used in Chemical Reactions:
2,6-Di-tert-butyl-4-methoxyphenol is also utilized in chemical reactions, specifically in In(trifluoromethanesulfonate)3-catalyzed tandem reactions with various nucleophiles. This application highlights its importance in the synthesis of complex organic compounds and contributes to the development of new materials and products in the chemical industry.

InChI:InChI=1/C15H24O2/c1-14(2,3)11-8-10(17-7)9-12(13(11)16)15(4,5)6/h8-9,16H,1-7H3

Synthetic route

Carbonic acid tert-butyl ester 2,6-di-tert-butyl-4-methoxy-phenyl ester → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 28h; Product distribution; deprotection;	100%

2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + methyl p-toluene sulfonate (80-48-8) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With sodium hydroxide at 90 - 100℃; for 1.5h;	93%

methanol (67-56-1) + 2,6-di-tert-butylphenol (128-39-2) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 4-bromo-2,6-di-tert-butylphenol (1139-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With bromine; silver perchlorate at 0℃; for 0.05h;	A 2% B 1% C 84%

4-(1-hydroxypropyl)-4-methoxy-2,6-di-t-butylcyclohexa-2,5-dienone (77074-15-8) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With sulfuric acid for 2h; Ambient temperature;	76%

4-bromo-2,6-di-tert-butyl-2,5-cyclohexadienone (950-57-2) → 2,6-di-tert-butylphenol (128-39-2) + 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 2,6-Di-tert-butyl-4-iodophenol (40084-31-9) + 4-bromo-2,6-di-tert-butylphenol (1139-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With iodine In methanol; water at 35℃; for 0.0833333h; Product distribution;	A 5% B 18% C 7% D 1% E 62% F 6%

2,4-di-t-butyl-4-bromophenol → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
sodium hydroxide In tetrahydrofuran; methanol	62%

(2,6-di-tert-butyl-4-methoxy-phenoxy)-acetic acid → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
Stage #1: (2,6-di-tert-butyl-4-methoxy-phenoxy)-acetic acid With diphenyl-phosphinic acid; triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius-rearrangement; Heating; Stage #2: With water In N,N-dimethyl-formamide; toluene Heating; Further stages.;	60%

methanol (67-56-1) + ethyl 3,5-di-tert-butyl-4-hydroxybenzoate (1620-64-0) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 3-tert-Butyl-4,5-dihydroxybenzoesaeure-ethylester (81056-45-3)

Conditions	Yield
With perchloric acid; sodium perchlorate anodic oxidation;	A 36% B 27% C 24%

ethyl 3,5-di-tert-butyl-4-hydroxybenzoate (1620-64-0) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 3-tert-Butyl-4,5-dihydroxybenzoesaeure-ethylester (81056-45-3)

Conditions	Yield
With methanol; perchloric acid; sodium perchlorate anodic oxidation;	A 36% B 27% C 24%

2,6-di-tert-butylphenol (128-39-2) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone (2455-14-3) + 2,6-Di-tert-butyl-4-iodophenol (40084-31-9) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 4,4'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl (128-38-1) + 4-methoxy-2,6-di-tert-butylcyclohexa-2,5-dienone

Conditions	Yield
With dihydrogen peroxide; iodine In methanol at 35℃; for 0.25h; Product distribution; Mechanism; other time 6-360 min;	A 3.6% B 2.9% C 6.6% D 5.7% E 2.4% F n/a

2,4,6-tri-tert-butyl-4-methoxy-2,5-cyclohexadienone (15910-49-3) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
at 250℃;

4-methoxy-phenol (150-76-5) + isobutene (115-11-7) → 3-tert-Butyl-4-hydroxyanisole (121-00-6) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With phosphoric acid

4-methoxy-phenol (150-76-5) + tert-butyl alcohol (75-65-0) → 3-tert-Butyl-4-hydroxyanisole (121-00-6) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With phosphoric acid

4-methoxy-phenol (150-76-5) → 2,5-di-tert-butyl-4-methoxyphenol (1991-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With sulfuric acid; Petroleum ether at 50℃; Einleiten von 2-Methyl-propen;

2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + dimethyl sulfate (77-78-1) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide; zinc Heating;

methanol (67-56-1) + 4-(1-methoxypropyl)-2,6-di-t-butylphenol (17540-78-2) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propan-1-one (14035-34-8)

Conditions	Yield
With hydrogen bromide; bromine for 18h; Mechanism; Ambient temperature; the same reaction , the same products/yield distribution for 4-(1-hydroxypropyl)-2,6-di-t-butylphenol (INO 760);	A 8 % Spectr. B 8 % Spectr. C 6 % Spectr.

methanol (67-56-1) + 2,6-di-t-butyl-4-bromo-4-(1-hydroxypropyl)cyclohexa-2,5-dienone (75697-72-2) → 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propan-1-one (14035-34-8)

Conditions	Yield
With sulfuric acid; water for 3.5h; Ambient temperature;	A 13 % Spectr. B 64 mg C 14 % Spectr.

methanol (67-56-1) + 2,6-di-t-butyl-4-bromo-4-(1-hydroxypropyl)cyclohexa-2,5-dienone (75697-72-2) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 4-(1-methoxypropyl)-2,6-di-t-butylphenol (17540-78-2) + 4-bromo-2,6-di-tert-butylphenol (1139-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propan-1-one (14035-34-8)

Conditions	Yield
With sulfuric acid for 3.5h; Product distribution; Mechanism; Ambient temperature; other percent H2SO4; other reaction times; the same reaction with water (25percent v/v); the same reaction with various reagents (allylic alcohol, AgNO3, HBr, LiI, Br2);	A 17 % Spectr. B 29 % Spectr. C 33 % Spectr. D 17 % Spectr. E 4 % Spectr.

2,6-di-tert-butyl-4-methoxyphenoxyl radical (20137-67-1, 3425-36-3) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 2,6-di-tert-butyl-4-methylphenoxy radical (6858-01-1, 24473-56-1)

Conditions	Yield
In toluene; benzene at -22.1 - 30.9℃; Equilibrium constant;
In benzene Equilibrium constant; Thermodynamic data; Ambient temperature; ΔG; also in tert-butanol;

2,6-di-tert-butyl-4-methoxyphenoxyl radical (20137-67-1, 3425-36-3) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With 2,6-di-tert-butyl-4-(3,5-di-tert-butyl-4-hydroxy-benzylidene)-cyclohexa-2,5-dienone In toluene at 24.9℃; Equilibrium constant;
With 2,6-di-tert-butyl-4-methyl-phenol In benzene at 19.85℃; Equilibrium constant; Thermodynamic data; Further Variations:; Solvents;

2,6-di-t-butyl-4-bromo-4-(1-hydroxypropyl)cyclohexa-2,5-dienone (75697-72-2) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 4-(1-methoxypropyl)-2,6-di-t-butylphenol (17540-78-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propan-1-one (14035-34-8)

Conditions	Yield
With methanol for 5h; Ambient temperature; Further byproducts given;	A 22 mg B 26 % Spectr. C 46 % Spectr. D 9 % Spectr.

2,6-di-t-butyl-4-bromo-4-(1-hydroxypropyl)cyclohexa-2,5-dienone (75697-72-2) → 4-(1-methoxypropyl)-2,6-di-t-butylphenol (17540-78-2) + 4-bromo-2,6-di-tert-butylphenol (1139-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-propan-1-one (14035-34-8)

Conditions	Yield
With methanol; sulfuric acid for 0.333333h; Ambient temperature; Further byproducts given;	A 3 % Spectr. B 120 mg C 2 % Spectr. D 4 % Spectr.

2,6-Di-tert-butyl-4-(1-hydroxyethyl)phenol (14681-20-0) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol

methanol (67-56-1) + 4-bromo-2,6-di-tert-butyl-2,5-cyclohexadienone (950-57-2) → 2,6-di-tert-butyl-4-hydroxyphenol (2444-28-2) + 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 4-bromo-2,6-di-tert-butylphenol (1139-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
With silver perchlorate; sodium carbonate at 0℃; for 0.0333333h; Yield given. Yields of byproduct given;

2,6-di-tert-butyl-4-methoxyphenoxyl radical (20137-67-1, 3425-36-3) + Tocopherol (59-02-9) → 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + α-tocopheroxyl radical (23531-69-3, 30970-82-2, 79645-40-2, 83376-94-7, 107081-04-9)

Conditions	Yield
In benzene Equilibrium constant; Thermodynamic data; Ambient temperature; ΔG; also in tert-butanol;
With di-tert-butyl peroxide In benzene at 24.85℃; Kinetics;

tertiary butyl chloride (507-20-0) + 4-methoxy-phenol (150-76-5) → 2,5-di-tert-butyl-4-methoxyphenol (1991-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
natural kaolinitic clay for 0.166667h; Alkylation; Heating; Title compound not separated from byproducts;
With lithium bromide for 1h; Heating;

sulfuric acid (7664-93-9) + 4-methoxy-phenol (150-76-5) + isobutene (115-11-7) + benzene (71-43-2) → 2,5-di-tert-butyl-4-methoxyphenol (1991-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
at 50 - 60℃;

sulfuric acid (7664-93-9) + 4-methoxy-phenol (150-76-5) + isobutene (115-11-7) + petroleum ether → 2,5-di-tert-butyl-4-methoxyphenol (1991-52-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

Conditions	Yield
at 50 - 60℃;

hydrogenchloride (7647-01-0) + 2,6-di-tert-butyl-4-methoxyphenoxyl radical (20137-67-1, 3425-36-3) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0)

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → 2,6-Di-tert-butyl-1,4-benzoquinone (719-22-2)

Conditions	Yield
With Nitrogen dioxide In dichloromethane for 0.0833333h; Ambient temperature;	100%
With dihydrogen peroxide; iodine In methanol at 35℃; for 0.833333h;	100%
With perchloric acid; lead dioxide In water; acetone at 25℃;	100%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + C40H99N13P4 → 2C15H24O2*C40H99N13P4

Conditions	Yield
In diethyl ether at 20℃; for 0.0833333h;	100%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + titanium tetrachloride (7550-45-0) → trichloromono(2,6-di-tert-butyl-4-methoxyphenoxide)titanium(IV) (263547-01-9)

Conditions	Yield
In toluene byproducts: HCl; under N2; 2,6-di-tert-butyl-4-methoxyphenol in toluene added to TiCl4 (molar ratio 1:1) in toluene; refluxed for 11 h; filtered; solvent removed; extended drying under vac.; elem. anal.;	99%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + C40H99N13P4 → C40H99N13P4*C15H24O2

Conditions	Yield
In diethyl ether for 1h;	98%
In diethyl ether at 20℃;	98%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + Ethyl oxalyl chloride (4755-77-5) → 2,6-di-tert-butyl-4-methoxyphenyl ethyl oxalate (609798-33-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h;	97%
With n-butyllithium In tetrahydrofuran at 0℃; Yield given;
With n-butyllithium In tetrahydrofuran at 0℃;

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 2,5-dimethoxybenzoic acid (2785-98-0) → 2,6-di-tert-butyl-4-methoxyphenyl 2,5-dimethoxybenzoate

Conditions	Yield
With trifluoroacetic anhydride In benzene Ambient temperature;	96%
In benzene at 20℃; for 7.5h;	92%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + acetic anhydride (108-24-7) → 4-acetoxy-3,5-di-tert-butylanisole (75169-17-4)

Conditions	Yield
copper(II) bis(tetrafluoroborate) at 20℃; for 0.5h;	95%
With sulfuric acid at 70℃; for 2h;	88%
With bismuth oxide perchlorate at 20℃; for 1h;	88%

methanol (67-56-1) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → 2,6-di-tert-butyl-4,4-dimethoxycyclohexa-2,5-dien-1-one (33974-39-9)

Conditions	Yield
With potassium hydroxide; iodine at 10℃; for 0.166667h;	93%
With thallium(III) nitrate

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + propionyl chloride (79-03-8) → 2',6'-bis(1",1"-dimethylethyl)-4'-methoxyphenyl propanoate (73198-88-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0℃;	93%
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: propionyl chloride In tetrahydrofuran at 20℃; for 2h;	84%
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: propionyl chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	53%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 2-6-dimethoxybenzoic acid (1466-76-8) → 2,6-di-tert-butyl-4-methoxyphenyl 2,6-dimethoxybenzoic acid ester (215023-79-3)

Conditions	Yield
With trifluoroacetic anhydride In benzene for 3h; Ambient temperature;	93%

[1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride (67292-34-6) + dichloromethane (75-09-2) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + nitrogen(II) oxide (10102-43-9) → [(((C6H5)2P)2(C5H4)2Fe)Ni(N2O2)]*0.5CH2Cl2

Conditions	Yield
In methanol; dichloromethane byproducts: 2,6-di-tertbutylbenzoquinone; metal complex in CH2Cl2 treated with ligand prepared in situ (2 equiv.) in methanol, evapd., crystd. at room temp.; filtered, washed (cold methanol), recrystd. (CH2Cl2/ethanol, room temp.), elem. anal.;	93%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + butyryl chloride (141-75-3) → 2',6'-bis(1",1"-dimethylethyl)-4'-methoxyphenyl butanoate (81818-79-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at 0℃;	92%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + isobutyryl chloride (79-30-1) → 2,6-di-tert-butyl-4-methoxyphenyl 2-methylpropanoate (486447-50-1)

Conditions	Yield
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: isobutyryl chloride In tetrahydrofuran at 20℃; for 2h;	90%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → 2H-O-2,6-di-tert-butyl-4-methoxyphenol (915404-01-2)

Conditions	Yield
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With dimethylsulfoxide-d6; sodium hydride for 16h; Stage #2: With water-d2	90%
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With ethyl [2]alcohol; sodium for 10h; Stage #2: With water-d2 Further stages.;
With water-d2 In acetone
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With n-butyllithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: With water-d2 In tetrahydrofuran; pentane at -78 - 20℃; Schlenk technique; Inert atmosphere;

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + tetra(n-butyl)ammonium hydroxide (2052-49-5) → C16H36N(1+)*C15H23O2(1-)

Conditions	Yield
In diethyl ether at 20℃; for 2h;	90%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → 4-acetoxy-3,5-di-tert-butylanisole (75169-17-4)

Conditions	Yield
With sodium bicarbonate; sulfuric acid In acetic anhydride	88%
With sulfuric acid; sodium hydrogencarbonate In acetic anhydride	88%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 2-Methoxybenzoic acid (579-75-9) → 2,6-di-tert-butyl-4-methoxyphenyl 2-methoxybenzoate (146017-93-8)

Conditions	Yield
With trifluoroacetic anhydride for 3h; Ambient temperature;	86%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → 2,6-di-tert-butyl-4-methoxyphenoxyl radical (20137-67-1, 3425-36-3)

Conditions	Yield
With ferrocenium hexafluorophosphate; C22H29CuN5O3(2-)*2C4H12N(1+) In N,N-dimethyl-formamide at -40℃; Reagent/catalyst; Inert atmosphere; Glovebox;	85%
With potassium hydroxide; diethyl ether; potassium hexacyanoferrate(III)
With lead dioxide; benzene

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-methoxy-2-naphthoic acid (883-21-6) → 1-Methoxy-naphthalene-2-carboxylic acid 2,6-di-tert-butyl-4-methoxy-phenyl ester (177606-84-7)

Conditions	Yield
With trifluoroacetic anhydride for 48h; Ambient temperature;	84%

di-tert-butyl dicarbonate (24424-99-5) + 2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → Carbonic acid tert-butyl ester 2,6-di-tert-butyl-4-methoxy-phenyl ester

Conditions	Yield
With dmap In hexane for 41h;	83%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 1-methoxy-2-naphthoyl chloride (51439-63-5) → 1-Methoxy-naphthalene-2-carboxylic acid 2,6-di-tert-butyl-4-methoxy-phenyl ester (177606-84-7)

Conditions	Yield
Stage #1: 2,6-Di-t-butyl-4-methoxyphenol With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: 1-methoxy-2-naphthoyl chloride In tetrahydrofuran at 0 - 20℃; Stage #3: With sodium hydroxide In tetrahydrofuran; water	82%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + acetonitrile (75-05-8) → N-tert-butylacetamide (762-84-5) + 2-methyl-5-methoxy-7-tert-butyl-1,3-benzoxazole (139656-58-9) + isobutene (115-11-7) + tert-butyl alcohol (75-65-0)

Conditions	Yield
With thianthrene cation radical perchlorate Further byproducts given;	A 31% B 80% C 6.3% D 39%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 2,2,6-trimethyl-4H-1,3-dioxin-4-one (5394-63-8) → 2,6-di-tert-butyl-4-methoxyphenyl 3-oxobutanoate

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; Inert atmosphere;	80%
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 2h; Inert atmosphere;

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → sodium (Z)-1-[4-(2,6-di-tert-butyl-4-methoxycyclohexadienonyl)]-diazen-1-ium-1,2-diolate

Conditions	Yield
With nitrogen(II) oxide; sodium In methanol at 20℃; under 1810.07 Torr; for 24h; Addition;	78%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) → 2,6-di-tert-butyl-4-methoxy-phenoxide tin (II)

Conditions	Yield
With bis(bis(trimethylsilyl)amido)tin(II) In toluene at 20℃; for 24h;	77%

2,6-Di-t-butyl-4-methoxyphenol (489-01-0) + 5-isopropoxy-2-methoxybenzoic acid (85686-11-9) → 5-isopropyl-2-methoxybenzoic acid 2,6-di-tert-butyl-4-methoxyphenyl ester (478705-41-8)

Conditions	Yield
With trifluoroacetic anhydride at 20℃; for 48h;	76%

Upstream product

• 15910-49-3 2,4,6-tri-tert-butyl-4-methoxy-2,5-cyclohexadienone 
• 150-76-5 4-methoxy-phenol 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 2444-28-2 2,6-di-tert-butyl-4-hydroxyphenol 
• 77-78-1 dimethyl sulfate 
• 67-56-1 methanol 
• 17540-78-2 4-(1-methoxypropyl)-2,6-di-t-butylphenol 
• 1620-64-0 ethyl 4-hydroxy-3,5-di-tert-butylbenzoate 
• 75697-72-2 4-bromo-4-(1-hydroxypropyl)-2,6-di-t-butylcyclohexa-2,5-dienone 
• 20137-67-1 2,6-di-tert-butyl-4-methoxyphenoxyl radical 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 80-48-8 methyl p-toluene sulfonate 
• 77074-15-8 4-(1-hydroxypropyl)-4-methoxy-2,6-di-t-butylcyclohexa-2,5-dienone 

Downstream Products

• 20137-67-1 2,6-di-tert-butyl-4-methoxyphenoxyl radical 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 33974-39-9 2,6-di-tert-butyl-4,4-dimethoxycyclohexa-2,5-dien-1-one 
• 125189-18-6 (4-methoxy-2,6-di-tert-butylphenoxy)oxalyl chloride 
• 52275-62-4 C₃₆H₅₀N₂O₆ 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 1975-15-1 2,6,2',6'-tetra-tert-butyl-4,4'-dimethoxy-4,4'-peroxy-bis-cyclohexa-2,5-dienone 
• 73198-88-6 2',6'-bis(1,1-dimethylethyl)-4'-methoxyphenyl propanoate 
• 75169-17-4 4-acetoxy-3,5-di-tert-butylanisole 
• 609798-33-6 2,6-di-tert-butyl-4-methoxyphenyl ethyl oxalate 
• 137569-34-7 4-Phenyl-butyric acid 2,6-di-tert-butyl-4-methoxy-phenyl ester 
• 81818-79-3 2',6'-bis(1,1-dimethylethyl)-4'-methoxyphenyl butanoate 
• 762-84-5 N-tert-butylacetamide 
• 139656-58-9 2-methyl-5-methoxy-7-tert-butyl-1,3-benzoxazole 

Relevant articles and documents

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