2409-55-4

Basic information

• Product Name: 2-tert-Butyl-4-methylphenol
• Synonyms: 1-Hydroxy-2-tert-butyl-4-methylbenzene;2-(1,1-dimethylethyl)-4-methyl-pheno;2-(1,1'-dimethylethyl)-4-methylphenol;2-(1,1-dimethylethyl)-4-methylphenol;2-(1,1-Dimethylethyl)-4-methyl-phenol;2-(1,1-Dimetyyletyly)-4-methylphenol;2-butyl-4-methylphenol;2-t-Butyl-4-methylphenol
• CAS NO: 2409-55-4
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.24
• EINECS: 219-314-6
• Product Categories: Industrial/Fine Chemicals;Organic intermediate;Antioxidant
• Mol File: 2409-55-4.mol
• Article Data: 39

Chemical Properties

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 244 °C(lit.)
• Flash Point: 212 °F
• Appearance: White to yellow-beige/Crystalline Mass
• Density: 0.92 g/cm3 (75℃)
• Vapor Pressure: 0.0299mmHg at 25°C
• Refractive Index: 1.4969
• Storage Temp.: Store below +30°C.
• Solubility: methanol: 0.1 g/mL, clear
• PKA: 11?+-.0.18(Predicted)
• Water Solubility: insoluble
• BRN: 1817645
• CAS DataBase Reference: 2-tert-Butyl-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-tert-Butyl-4-methylphenol(2409-55-4)
• EPA Substance Registry System: 2-tert-Butyl-4-methylphenol(2409-55-4)

Safety Data

• Hazard Codes: C,N
• Statements: 34-37-51/53
• Safety Statements: 26-36/37/39-45-61-29-20
• RIDADR: UN 2430 8/PG 3
• WGK Germany: 2
• RTECS: GO7000000
• F: 8-9-23
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2409-55-4(Hazardous Substances Data)

Usage

Chemical Properties

white to yellow-beige crystalline mass

Safety Profile

A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and skin contact. Questionable carcinogen with experimental neoplastigenic data. A severe skin and eye irritant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, foam, water spray, fog, dry chemical. When heated to decomposition it emits acrid and irritating fumes.

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

Synthetic route

p-cresol (106-44-5) + tert-butyl alcohol (75-65-0) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
at 70℃; for 8h; Kinetics; Concentration; Reagent/catalyst; Temperature; Time; Friedel-Crafts alkylation; Ionic liquid; Autoclave; regioselective reaction;	A 90% B 9.5%
With carbon tetrabromide at 175℃; for 6h; Sealed tube;	A 68% B 29%
With carbon tetrabromide at 175℃; for 6h; Sealed tube;	A 62% B 38%
1-butyl-3-methylimidazolium heptachlorodiindate (III) at 110℃; for 4h; Product distribution / selectivity; In ionic liquid;
With multi-walled carbon nanotubes supported on SO3H In neat (no solvent) for 10h; Reagent/catalyst; Reflux;	A 85.6 %Chromat. B 6.7 %Chromat.

2-tert-butyl-4-methyl-1-(2-phenylallyloxy)benzene → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h;	88%

p-cresol (106-44-5) + tert-butyl alcohol (75-65-0) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With sulfated zirconia at 140℃; for 1h;	86%
With phosphoric acid at 85 - 90℃;
With sulfuric acid at 60℃;

Carbonic acid tert-butyl ester 2-tert-butyl-4-methyl-phenyl ester → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane for 3h; Product distribution; Heating; deprotection;	85%

2-(tert-butyl)-4-hydroxy-4-methylcyclohexa-2,5-dien-1-one → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With sodium hydride; bis(pinacol)diborane In 1,2-dichloro-ethane at 70℃; for 12h; Inert atmosphere;	71%

tert.-butylhydroperoxide (75-91-2) + p-cresol (106-44-5) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With iron(III) chloride In tetrachloromethane at 80℃; for 4h; Alkylation;	67%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
at 300℃; for 12h;	55%
at 300℃; for 12h; Product distribution; 270 deg C, 6 h;;	55%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + acetonitrile (75-05-8) → N-tert-butylacetamide (762-84-5) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,5-dimethyl-7-tert-butyl-1,3-benzoxazole (139656-59-0) + tert-butyl alcohol (75-65-0)

Conditions	Yield
With thianthrene cation radical perchlorate Further byproducts given;	A 18% B 5.6% C 43% D 53%

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + phenol (108-95-2) → p-cresol (106-44-5) + para-tert-butylphenol (98-54-4) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butylphenol (128-39-2) + 2-tert-Butylphenol (88-18-6) + 2,4-di-tert-Butylphenol (96-76-4)

Conditions	Yield
C24H20ClNbO4 at 140℃; for 3h; Product distribution; Rate constant; Mechanism; also with 2-methylphenol, other catalysts, other products;	A 14% B 8% C 30.5% D 2% E 20% F 15%

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%

tert-Butyl-(2-tert-butyl-4-methyl-phenoxy)-dimethyl-silane → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II) In water; acetone at 75℃; for 48h;	10%

p-cresol (106-44-5) + tertiary butyl chloride (507-20-0) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
at 45℃; Kinetics;

4-(tert-butoxy)toluene (15359-98-5) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
With sulfuric acid at 90℃;

p-cresol (106-44-5) + isobutene (115-11-7) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
AShNTs-3 zeolite at 239.9 - 269.9℃; Equilibrium constant; Thermodynamic data;
With acid ion exchanger
With aluminium tris(p-methylphenoxide)
With sulfuric acid
With zeolite catalyst H-USY at 80℃; for 8h;

p-cresol (106-44-5) + isobutene (115-11-7) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
With sulfuric acid; glycerol at 20 - 100℃;
With sulfuric acid; glycerol at 70℃;
With acidic ion exchanger

p-cresol (106-44-5) + para-tert-butylphenol (98-54-4) → 2-tert-Butyl-4-methylphenol (2409-55-4) + phenol (108-95-2)

Conditions	Yield
cation-exchangers KU-23; protonic acid at 129.9℃; Equilibrium constant; diff. temp.;

p-cresol (106-44-5) + 2,4-di-tert-Butylphenol (96-76-4) → para-tert-butylphenol (98-54-4) + 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
cation-exchangers KU-23; protonic acid at 129.9℃; Equilibrium constant; diff. temp.;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → p-cresol (106-44-5) + 2-tert-Butyl-4-methylphenol (2409-55-4) + isobutene (115-11-7)

Conditions	Yield
With phosphotungstic acid In acetic acid at 140℃; Rate constant; Product distribution; other temperatures, solvents, catalysts; catalysis of dealkylation of 2,6-di-tert-butylphenol derivatives by heteropoly acids;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + ortho-cresol (95-48-7) → p-cresol (106-44-5) + 2-Methyl-4-t-butylphenol (98-27-1) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2-tert-Butyl-6-methylphenol (2219-82-1)

Conditions	Yield
C24H20ClNbO4 at 140℃; for 3h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + ortho-cresol (95-48-7) → p-cresol (106-44-5) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2-tert-Butyl-6-methylphenol (2219-82-1) + 2,4-di-tert-butyl-6-methylphenol (616-55-7)

Conditions	Yield
sulfuric acid at 80℃; for 8h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + ortho-cresol (95-48-7) → 2-Methyl-4-t-butylphenol (98-27-1) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2-tert-Butyl-6-methylphenol (2219-82-1) + 2,4-di-tert-butyl-6-methylphenol (616-55-7)

Conditions	Yield
sulfuric acid at 80℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given;
sulfuric acid at 80℃; for 2h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + phenol (108-95-2) → p-cresol (106-44-5) + para-tert-butylphenol (98-54-4) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,4-di-tert-Butylphenol (96-76-4)

Conditions	Yield
C24H20ClNbO4 at 140℃; for 3h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + phenol (108-95-2) → p-cresol (106-44-5) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2-tert-Butylphenol (88-18-6) + 2,4-di-tert-Butylphenol (96-76-4)

Conditions	Yield
C24H20ClNbO4 at 140℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given;
C24H20ClNbO4 at 140℃; for 3h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + phenol (108-95-2) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butylphenol (128-39-2) + 2-tert-Butylphenol (88-18-6) + 2,4-di-tert-Butylphenol (96-76-4)

Conditions	Yield
C24H20ClNbO4 at 140℃; for 1h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + phenol (108-95-2) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2-tert-Butylphenol (88-18-6) + 2,4-di-tert-Butylphenol (96-76-4) + 2,4,6-tri-tert-butylphenoxol (732-26-3)

Conditions	Yield
C24H20ClNbO4 at 140℃; for 0.25h; Yield given. Further byproducts given. Yields of byproduct given;

2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → p-cresol (106-44-5) + 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
aluminum(III) sulfate at 139.9℃; for 8h; Product distribution; Mechanism; other catalysts, var. temp. and time;	A 14.4 % Chromat. B 61.4 % Chromat.

2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane (119-47-1) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
at 120℃; other bisphenols; thermo-oxidative stability; var. temperature;

p-cresol (106-44-5) + phosphoric acid (86119-84-8, 7664-38-2) + tert-butyl alcohol (75-65-0) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
at 60 - 70℃;

p-cresol (106-44-5) + sulfuric acid (7664-93-9) + water (7732-18-5) + tert-butyl alcohol (75-65-0) → 2-tert-Butyl-4-methylphenol (2409-55-4)

Conditions	Yield
at 60℃;

p-cresol (106-44-5) + sulfuric acid (7664-93-9) + isobutene (115-11-7) → 2-tert-Butyl-4-methylphenol (2409-55-4) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0)

Conditions	Yield
at 60 - 70℃;

2-tert-Butyl-4-methylphenol (2409-55-4) + C25H26ClN2OP (94669-45-1, 94669-46-2) → C36H41N2O2P

Conditions	Yield
With triethylamine at -76℃;	100%

2-tert-Butyl-4-methylphenol (2409-55-4) + C25H26ClN2OP (94669-47-3, 94669-48-4, 76085-17-1) → C36H41N2O2P

Conditions	Yield
With triethylamine at -76℃;	100%

2-tert-Butyl-4-methylphenol (2409-55-4) → 2-(tert-butyl)-6-chloro-4-methylphenol (13395-07-8)

Conditions	Yield
With N-chloro-succinimide; triphenylphosphine sulfide In dichloromethane at 20℃; for 12h;	100%
With sulfuryl dichloride In chloroform for 24h; Ambient temperature;	71%

2-tert-Butyl-4-methylphenol (2409-55-4) → 2-bromo-6-tert-butyl-4-methylphenol (1516-93-4)

Conditions	Yield
With bromine In dichloromethane at 20℃; for 2h;	100%
With bromine In dichloromethane at 0 - 20℃; for 2h;	100%
With bromine; acetic acid In chloroform Inert atmosphere;	98%

2-tert-Butyl-4-methylphenol (2409-55-4) + [6-Hydroxy-2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-5-yl]methyl bromide (187806-29-7) → 5a-(3-tert-butyl-2-hydroxy-5-methyl-phenyl)-α-tocopherol

Conditions	Yield
With hydrogen bromide; zinc(II) chloride In hexane; dichloromethane at 50℃; for 4h;	100%

2-tert-Butyl-4-methylphenol (2409-55-4) + di-tert-butyl dicarbonate (24424-99-5) → Carbonic acid tert-butyl ester 2-tert-butyl-4-methyl-phenyl ester

Conditions	Yield
With dmap In hexane for 0.333333h;	100%

2-tert-Butyl-4-methylphenol (2409-55-4) + diethyl chlorophosphate (814-49-3) → phosphoric acid 2-tert-butyl-4-methylphenyl ester diethyl ester (952665-30-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.75h;	100%
With ammonium chloride In tetrahydrofuran; mineral oil
Stage #1: 2-tert-Butyl-4-methylphenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: diethyl chlorophosphate In tetrahydrofuran; mineral oil at 0 - 25℃; for 0.5h;
Stage #1: 2-tert-Butyl-4-methylphenol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: diethyl chlorophosphate In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h;

2-tert-Butyl-4-methylphenol (2409-55-4) + chloromethyl methyl ether (107-30-2) → 1-methoxymethoxy-2-tert-butyl-4-methylbenzene (150094-87-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 3h;	99%
With sodium hydride

titanium(IV) isopropylate (546-68-9) + 2-tert-Butyl-4-methylphenol (2409-55-4) → [(2-tert-butyl-4-methylphenoxy)Ti(isopropoxy)3]

Conditions	Yield
In cyclohexane at 20℃; Inert atmosphere; Schlenk technique;	99%

titanium(IV) isopropylate (546-68-9) + 2-tert-Butyl-4-methylphenol (2409-55-4) → [(2-tert-butyl-4-methylphenoxy)2Ti(isopropoxy)2] (259856-05-8)

Conditions	Yield
In cyclohexane at 20℃; Inert atmosphere; Schlenk technique;	99%

3,4-dihydro-2H-pyran (110-87-2) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 2-(2-tert-butyl-4-methylphenoxy)tetrahydro-2H-pyran

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 0 - 20℃; Inert atmosphere;	99%
Stage #1: 2-tert-Butyl-4-methylphenol With toluene-4-sulfonic acid In dichloromethane for 0.0166667h; Inert atmosphere; Glovebox; Stage #2: 3,4-dihydro-2H-pyran In dichloromethane Time; Inert atmosphere; Glovebox;	94%

1-methyl-piperazine (109-01-3) + formaldehyd (50-00-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) → (N-piperazinyl-N′-methyl)-2-methylene-4-methyl-6-tert-butylphenol (1356094-48-8)

Conditions	Yield
In water for 18h; Reflux; Inert atmosphere;	98%

2-tert-Butyl-4-methylphenol (2409-55-4) + propargyl bromide (106-96-7) → 2-tert-butyl-4-methyl-1-(prop-2-ynyloxy)benzene (886997-85-9)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In toluene at 35 - 40℃; for 4h;	97.2%

Dimethoxymethane (109-87-5) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane (119-47-1)

Conditions	Yield
With acid clay at 170℃; for 2h; Reagent/catalyst; Temperature;	97%
With sulfuric acid at 60 - 70℃; for 2h;	70%
With cation exchanger KU-2; sulfuric acid at 100℃; for 3h; Kinetics; Mechanism; Rate constant; other time, other temperature;

2-tert-Butyl-4-methylphenol (2409-55-4) + acetic anhydride (108-24-7) → 2-t-butyl-4-methylphenyl acetate

Conditions	Yield
With zirconium sulfophenyl phosphonate In dichloromethane at 20℃; for 12h; Acetylation;	97%

iodobenzene (591-50-4) + 2-tert-Butyl-4-methylphenol (2409-55-4) + carbon monoxide (201230-82-2) → C18H20O2 (60170-87-8)

Conditions	Yield
With triethylamine; palladium on activated charcoal In toluene at 130℃; under 15001.5 Torr; for 8h; Sonogashira coupling;	97%

tetrahydrofuran (109-99-9) + 2-tert-Butyl-4-methylphenol (2409-55-4) + titanium tetrachloride (7550-45-0) → [2-tert-butyl-4-methylphenolateTi(IV)Cl3(THF)]

Conditions	Yield
In toluene at -78 - 65℃; for 8h; Inert atmosphere;	97%

2-tert-Butyl-4-methylphenol (2409-55-4) + indan-1,2,3-trione hydrate (485-47-2) → 2-(3-tert-Butyl-2-hydroxy-5-methyl-phenyl)-2-hydroxy-indan-1,3-dione (71313-39-8)

Conditions	Yield
In acetic acid for 0.5h; Heating;	96%

tert.-butylhydroperoxide (75-91-2) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 3,3′- di-tert-butyl-5,5′-dimethyl-[1,1′-biphenyl]-2,2′-diol (6390-59-6)

Conditions	Yield
With iron(III) chloride In tetrachloromethane at 80℃; for 4h; Alkylation; dimerization;	96%

formaldehyd (50-00-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane (119-47-1)

Conditions	Yield
With sodium tetramethoxyborate In dimethyl sulfoxide at 150℃; for 0.5h; Reagent/catalyst; Temperature; Solvent;	95%
In xylene at 175℃; for 10h;	85%
With montmorillonite KSF In octane for 2h; Reflux;	79%

formaldehyd (50-00-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 3-tert-butyl-5-methylsalicylaldehyde (41715-31-5)

Conditions	Yield
In acetonitrile at 100 - 110℃; for 2h; Inert atmosphere;	95%
Stage #1: 2-tert-Butyl-4-methylphenol With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 1h; Stage #2: formaldehyd With triethylamine In tetrahydrofuran; toluene at 70℃; for 1h;	72%
With Montmorillonite KSF; triethylamine In toluene at 100℃; for 4h; Formylation;	67%

2-tert-Butyl-4-methylphenol (2409-55-4) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → (2-tert-Butyl-4-methyl-phenoxy)-trimethyl-silane (134291-10-4)

Conditions	Yield
With zirconium sulfophenyl phosphonate In dichloromethane for 0.5h; Ambient temperature;	95%
With [nano-MCM-41(at)(CH2)3-1-methylimidazole]Br3 In dichloromethane at 20℃; for 1.16667h;	93%
With poly(4-vinylpyridinium tribromide) In acetonitrile at 20℃; for 0.0666667h;	99 %Chromat.

formaldehyd (50-00-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) + 2-methoxyethylamine (109-85-3) → 2-methoxyethylamino-N,N-bis(2-methylene-4-methyl-6-tert-butylphenol) (1033002-95-7)

Conditions	Yield
In water for 12h; Mannich reaction; Reflux;	95%
In water for 12h; Reflux;	95%
In water at 100℃; for 18h; Mannich reaction;	88%
In water for 24h; Reflux;	84%
In methanol; water Mannich condensation; Heating;

(2-aminomethylpyridine) (3731-51-9) + formaldehyd (50-00-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) → N,N-bis[methyl(2-hydroxy-3-tert-butyl-5-methylphenyl)]-aminomethylpyridine (1033002-91-3)

Conditions	Yield
With water for 12h; Heating;	95%
In water for 48h; Reflux;	73%
In water at 100℃; for 18h; Mannich reaction;	55%
In methanol for 24h; Mannich condensation; Heating;	55%
In methanol; water for 24h; Reflux;	28%

iodobenzene (591-50-4) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 2-(tert-butyl)-4-methyl-1-phenoxybenzene (1353547-71-3)

Conditions	Yield
With copper(I) oxide; caesium carbonate; imidazole-4-carboxylic acid In acetonitrile at 80℃; for 24h;	94%

1,1-Diphenylmethanol (91-01-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 2-benzhydryl-6-tert-butyl-4-methylphenol

Conditions	Yield
With sulfuric acid; acetic acid	94%

2-tert-Butyl-4-methylphenol (2409-55-4) + hexamethylenetetramine (100-97-0) → 2-tert-butyl-4-methyl-6-[(6-tert-butyl-8-methyl-2H-1,3-benzoxazin-3(4H)-yl)methyl]phenol (91432-07-4)

Conditions	Yield
at 175℃; melt;	93.8%

1,4-Diazacycloheptane (505-66-8) + formaldehyd (50-00-0) + 2-tert-Butyl-4-methylphenol (2409-55-4) → 1,4-bis(3-tert-butyl-5-methyl-2-hydroxybenzyl)-1,4-diazacycloheptane (503540-53-2)

Conditions	Yield
In water for 24h; Mannich Aminomethylation; Inert atmosphere; Schlenk technique; Reflux;	93.6%
Stage #1: 1,4-Diazacycloheptane; formaldehyd In methanol for 1h; Heating; Stage #2: 2-tert-Butyl-4-methylphenol In methanol for 24h; Mannich reaction; Heating;	50%
In methanol; water for 24h; Mannich reaction; Reflux; Inert atmosphere;

1,3-Benzothiazole (95-16-9) + 2-tert-Butyl-4-methylphenol (2409-55-4) + benzyl bromide (100-39-0) → 2-tert-butyl-6-(3-benzyl-2,3-dihydrobenzo[d]thiazol-2-yl)-4-methylphenol

Conditions	Yield
Stage #1: 1,3-Benzothiazole; benzyl bromide In acetonitrile for 2h; Reflux; Stage #2: 2-tert-Butyl-4-methylphenol With triethylamine In acetonitrile for 3h; Reflux;	93%

2-tert-Butyl-4-methylphenol (2409-55-4) → 2-(1,1-dimethylethyl)-4-methyl cyclohexanol (67634-11-1)

Conditions	Yield
With potassium hydroxide; Raney Ni-Al; water at 90℃; for 18h;	92%
With nickel at 160 - 190℃; Hydrogenation; optically inactive stereoisomer(ic) of bp : 216 degree;
With sodium 2-tert-butyl-4-methylphenolate; nickel at 220℃; Hydrogenation; optically inactive stereoisomer(ic) of bp : 216 degree;

Upstream product

• 106-44-5 p-cresol 
• 507-20-0 tertiary butyl chloride 
• 15359-98-5 4-(tert-butoxy)toluene 
• 115-11-7 isobutene 
• 75-65-0 tert-butyl alcohol 
• 98-54-4 para-tert-butylphenol 
• 96-76-4 2,4-di-tert-Butylphenol 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 95-48-7 ortho-cresol 
• 105-67-9 2,4-Xylenol 
• 75-05-8 acetonitrile 
• 108-95-2 phenol 
• 7664-93-9 sulfuric acid 
• 1516-93-4 2-bromo-6-tert-butyl-4-methylphenol 

Downstream Products

• 119-47-1 2,2'-dihydroxy-5,5'-dimethyl-3,3'-di-tert-burtyl-1,1'-diphenylmethane 
• 25844-12-6 2-hydroxy-5-methyl-3-tert-butylbenzyl alcohol 
• 90-68-6 2,6-bis[[3-(1,1-dimethylethyl)-2-hydroxy-5-methylphenyl]methyl]-4-methyl-phenol 
• 90-66-4 2,2-thiobis(4-methyl-6-tert-butylphenol) 
• 67634-11-1 2-(1,1-dimethylethyl)-4-methyl cyclohexanol 
• 70444-48-3 6-tert-butyl-4-methyl-2-nitrosophenol 
• 49592-92-9 3-tert-butyl-2-hydroxy-5-methylbenzyl chloride 
• 41028-29-9 2-oxapropanediyl-1,3-bis(2-tert-butyl-4-methylphenol) 
• 17619-06-6 6,6-(phenylmethylene)bis(2-(tert-butyl)4-methylphenol) 
• 4773-40-4 6,6'-di-tert-butyl-4,4'-dimethyl-2,2'-ethylidene-di-phenol 
• 3674-01-9 allyl-(2-tert-butyl-4-methyl-phenyl)-ether 
• 93803-56-6 6,6'-di-tert-butyl-4,4'-dimethyl-2,2'-isobutylidene-di-phenol 
• 4809-85-2 6,6'-di-tert-butyl-4,4'-dimethyl-2,2'-isopropylidene-di-phenol 
• 101940-69-6 methylamino-N,N-bis(6-tert-butyl-4-methyl-2-methylenephenol) 

Relevant articles and documents

Method for preparing 2-tert-butyl p-cresol under catalysis of eutectic solvent

The invention discloses a method for preparing 2-tert-butyl p-cresol under catalysis of a deep-eutectic solvent, which comprises the following steps: (1) taking caprolactam as a hydrogen bond acceptor and p-toluenesulfonic acid as a hydrogen bond donor, and reacting under a stirring condition to prepare the deep-eutectic solvent; and (2) accurately weighing methylphenol and tert-butyl alcohol according to a molar ratio of (12-5): (1-3), putting the weighed methylphenol and tert-butyl alcohol into a reaction tube, adding the eutectic solvent into the reaction tube, and stirring at 25-50 DEG C for 3-8 hours to obtain the 2-tert-butyl p-cresol. According to the method, the eutecticevaporate solvent taking p-toluenesulfonic acid as a hydrogen bond donor and caprolactam as a hydrogen bond acceptor is adopted to catalyze the alkylation reaction of p-methylphenol and tert-butyl alcohol, and the catalytic activity of the eutecticevaporate solvent can be optimal by accurately controlling all parameters in the alkylation of p-methylphenol; according to the method, the conversion rate of the tert-butyl alcohol can reach the maximum value of 100%, the selectivity of the 2-tert-butyl p-cresol can reach 99%, and the reaction does not corrode equipment, so that the method has a wide application prospect.

Enantioselective Kinetic Resolution/Desymmetrization of Para-Quinols: A Case Study in Boronic-Acid-Directed Phosphoric Acid Catalysis

A chiral phosphoric acid-catalyzed kinetic resolution and desymmetrization of para-quinols operating via oxa-Michael addition was developed and subsequently subjected to mechanistic study. Good to excellent s-factors/enantioselectivities were obtained over a broad range of substrates. Kinetic studies were performed, and DFT studies favor a hydrogen bonding activation mode. The mechanistic studies provide insights to previously reported chiral anion phase transfer reactions involving chiral phosphate catalysts in combination with boronic acids. (Figure presented.).