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3549-23-3

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3549-23-3 Usage

Description

Methyl p-tert-butylphenylacetate has a sweet, woody, and camphoraceous odor with a roasted, chocolate-like flavor. May be prepared by esterification of p-tert-butylphenylacetic acid with methanol.

Chemical Properties

Methyl p-tert-butylphenylacetate has a sweet, woody and camphoraceous odor and a roasted, chocolate-like flavor.

Preparation

By esterification of p-tert-butylphenylacetic acid with methanol

Aroma threshold values

Aroma characteristics at 1.0%: musty meaty, chicken fatty, cocoa honey, floral, sour, fatty milky, dairy and fishy nuances.

Taste threshold values

Taste characteristics at 5 ppm: leafy, green, waxy and honey-like, sweet cocoa, buttery creamy, fatty milky dairy-like with fishy and fruity nuances

General Description

Methyl p-tert-butylphenylacetate can be used as a food flavoring agent.

Check Digit Verification of cas no

The CAS Registry Mumber 3549-23-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,4 and 9 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3549-23:
(6*3)+(5*5)+(4*4)+(3*9)+(2*2)+(1*3)=93
93 % 10 = 3
So 3549-23-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H18O2/c1-13(2,3)11-7-5-10(6-8-11)9-12(14)15-4/h5-8H,9H2,1-4H3

3549-23-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A12421)  Methyl 4-tert-butylphenylacetate, 97%   

  • 3549-23-3

  • 5g

  • 586.0CNY

  • Detail
  • Alfa Aesar

  • (A12421)  Methyl 4-tert-butylphenylacetate, 97%   

  • 3549-23-3

  • 25g

  • 1509.0CNY

  • Detail
  • Alfa Aesar

  • (A12421)  Methyl 4-tert-butylphenylacetate, 97%   

  • 3549-23-3

  • 100g

  • 5066.0CNY

  • Detail

3549-23-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl p-tert-butylphenylacetate

1.2 Other means of identification

Product number -
Other names METHYLPARA-TERT-BUTYLPHENYLACETATE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3549-23-3 SDS

3549-23-3Synthetic route

methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

4-(1,1-dimethylethyl)-benzenemethanamine
39895-55-1

4-(1,1-dimethylethyl)-benzenemethanamine

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); carbonic acid dimethyl ester; 1,4-di(diphenylphosphino)-butane at 140℃; for 24h; Inert atmosphere;74%
methanol
67-56-1

methanol

4-tert-butylbenzyl cyanide
3288-99-1

4-tert-butylbenzyl cyanide

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid Hydrolysis; Esterification;
4-tert-butylbenzyl chloride
19692-45-6

4-tert-butylbenzyl chloride

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O / methanol
2: p-TsOH*H2O
View Scheme
methanol
67-56-1

methanol

4-t-butylphenylacetic acid
32857-63-9

4-t-butylphenylacetic acid

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

Conditions
ConditionsYield
With sulfuric acid In methanol for 5h; Reflux;
With thionyl chloride at 60℃; for 0.5h; Cooling with ice;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-t-butylphenylacetic acid
32857-63-9

4-t-butylphenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; methanol; water at 23℃; for 12h;100%
With sodium hydroxide In methanol; water at 20℃;39%
With sodium hydroxide In methanol
LiOH monohydrate

LiOH monohydrate

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-t-butylphenylacetic acid
32857-63-9

4-t-butylphenylacetic acid

Conditions
ConditionsYield
With sulfuric acid In methanol; water99%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2-(4-tert-butylphenyl)ethanol
5406-86-0

2-(4-tert-butylphenyl)ethanol

Conditions
ConditionsYield
With C15H29MnNO3P2(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 110℃; under 22502.3 Torr; for 24h; Inert atmosphere; Autoclave;95%
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;94%
With lithium aluminium tetrahydride In diethyl ether for 0.5h; Reduction; Heating;87%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With iron (II) stearate; ethylenediamine In toluene at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
Stage #2: In toluene at 100℃; for 20h; Inert atmosphere; Schlenk technique;
81%
With diisobutylaluminium hydride In dichloromethane; toluene at -20 - 20℃;72%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

1-(4-(tert-butyl)benzyl)cyclopropanol
1439386-58-9

1-(4-(tert-butyl)benzyl)cyclopropanol

Conditions
ConditionsYield
With titanium(IV) isopropylate In tetrahydrofuran at 0 - 20℃; for 0.666667h; Kulinkovich Hydroxycyclopropanation; Inert atmosphere;90%
With titanium(IV) isopropylate at 0℃; for 0.5h; Kulinkovich Hydroxycyclopropanation; Inert atmosphere;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl iodide
74-88-4

methyl iodide

(+/-)-2-(4-tert-butylphenyl)propionic acid methyl ester
154320-48-6

(+/-)-2-(4-tert-butylphenyl)propionic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran at -70 - 20℃; for 16.0833h;
89%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.333333h;
Stage #2: methyl iodide In tetrahydrofuran; hexane at 0℃; for 0.5h;
86%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: methyl iodide In tetrahydrofuran at -78℃; for 2h; Further stages.;
With lithium hexamethyldisilazane In tetrahydrofuran; hexane; water; ethyl acetate2.65 g (53%)
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2-(4-(tert-butyl)phenyl)acetohydrazide

2-(4-(tert-butyl)phenyl)acetohydrazide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol Reflux;88%
With hydrazine hydrate In methanol at 50℃; for 2h;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-(tert-butyl)phenyl)-2-oxoacetate
1034854-37-9

methyl 2-(4-(tert-butyl)phenyl)-2-oxoacetate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With tert.-butylhydroperoxide; copper(II) oxide In water at 110℃; for 4.5h;
Stage #2: With pyridine In water at 50℃; for 4h;
85%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-(1,1-Dimethylethyl)phenylmethyl ketone
64321-35-3

4-(1,1-Dimethylethyl)phenylmethyl ketone

Conditions
ConditionsYield
With sodium hydride In toluene; mineral oil at 20 - 75℃; for 1.83333h; Schlenk technique; Inert atmosphere;83.5%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With sodium hydride In toluene; mineral oil at 75℃; for 2.5h; Schlenk technique;
Stage #2: With hydrogenchloride; water; acetic acid at 130℃;
70%
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With sodium hydride In toluene at 75℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: With hydrogenchloride; acetic acid In water at 130℃; for 18h; Schlenk technique; Inert atmosphere;
52%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

propargyl bromide
106-96-7

propargyl bromide

methyl 2-(4-(tert-butyl)phenyl)-2-(prop-2-yn-1-yl)pent-4-ynoate

methyl 2-(4-(tert-butyl)phenyl)-2-(prop-2-yn-1-yl)pent-4-ynoate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere;
Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil at 0 - 20℃; for 16h; Inert atmosphere;
83%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

A

(E)-methyl 3-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)phenyl)acrylate

(E)-methyl 3-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)phenyl)acrylate

B

(2E,2'E)-dimethyl 3,3'-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)-1,3-phenylene)diacrylate

(2E,2'E)-dimethyl 3,3'-(5-(tert-butyl)-2-(2-methoxy-2-oxoethyl)-1,3-phenylene)diacrylate

Conditions
ConditionsYield
With (S)-acetamidoalanine; palladium diacetate; silver nitrate at 80℃; for 6h; chemoselective reaction;A 81%
B 13%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

benzaldehyde
100-52-7

benzaldehyde

syn-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

syn-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

anti-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

anti-methyl 2-(4-tert-butylphenyl)-3-hydroxy-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: benzaldehyde In dichloromethane at 20℃; for 3h; Aldol Condensation; Inert atmosphere; Overall yield = 90percent; diastereoselective reaction;
A 78%
B n/a
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With triethylamine; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane In dichloromethane at -78℃; for 2h; Inert atmosphere;
Stage #2: benzaldehyde In dichloromethane at -78℃; for 3h; Aldol Condensation; Inert atmosphere; Overall yield = 67percent; diastereoselective reaction;
A n/a
B 61%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

dimethyl sulfate
77-78-1

dimethyl sulfate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

methyl 3-methoxy-2-(4-tert-butylphenyl)acrylate

methyl 3-methoxy-2-(4-tert-butylphenyl)acrylate

Conditions
ConditionsYield
Stage #1: trimethyl orthoformate With titanium tetrachloride In 1,2-dichloro-ethane at 10 - 20℃; for 1h; Inert atmosphere;
Stage #2: methyl 2-(4-tert-butylphenyl)acetate In 1,2-dichloro-ethane at 0 - 20℃; for 2h; Inert atmosphere;
Stage #3: dimethyl sulfate Further stages;
77.5%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

d5-ethylmagnesium bromide
5780-97-2

d5-ethylmagnesium bromide

C14H16(2)H4O

C14H16(2)H4O

Conditions
ConditionsYield
With titanium(IV) isopropylate In tetrahydrofuran Inert atmosphere;76%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-bromo-2-(4-(tert-butyl)phenyl)acetate
77053-60-2

methyl 2-bromo-2-(4-(tert-butyl)phenyl)acetate

Conditions
ConditionsYield
With N-Bromosuccinimide; hydrogen bromide In tetrachloromethane Heating;65%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In chloroform at 60℃; for 1h;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

4-(2-(4-(tert-butyl)phenyl)acetamido)benzoic acid

4-(2-(4-(tert-butyl)phenyl)acetamido)benzoic acid

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran; n-heptane at 125℃; for 0.666667h; Microwave irradiation;65%
Estragole
140-67-0

Estragole

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

C22H28O2

C22H28O2

Conditions
ConditionsYield
With titanium(IV) isopropylate; cyclohexylmagnesiumchloride In tetrahydrofuran; diethyl ether at 20℃; for 1.66667h; Kulinkovich Hydroxycyclopropanation; Inert atmosphere;61%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2,2'-(2-(4-(tert-butyl)phenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

2,2'-(2-(4-(tert-butyl)phenyl)ethane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions
ConditionsYield
With ethanol; iron(II) bromide; sodium t-butanolate In toluene at 100℃; for 24.0833h; Inert atmosphere; Glovebox;60%
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-trifluoromethylphenyl)-2-diazoacetate
1313370-94-3

methyl 2-(4-trifluoromethylphenyl)-2-diazoacetate

Conditions
ConditionsYield
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; Inert atmosphere;51%
With 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; for 12h;
With 4-toluenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 0 - 20℃; Inert atmosphere;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde
185040-32-8

4-methylamino-2-methylthiopyrimidine-5-carboxaldehyde

6-(4-(tert-butyl)phenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

6-(4-(tert-butyl)phenyl)-8-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Conditions
ConditionsYield
With potassium fluoride on basic alumina In N,N-dimethyl acetamide at 20℃; for 3h; Inert atmosphere;41%
Trifluoromethanesulfonamide
421-85-2

Trifluoromethanesulfonamide

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-(tert-butyl)phenyl)-2-((trifluoromethyl)sulfonamido)acetate

methyl 2-(4-(tert-butyl)phenyl)-2-((trifluoromethyl)sulfonamido)acetate

Conditions
ConditionsYield
With bis(4-bromobenzoyloxy)iodobenzene; iodine In dichloromethane at 20℃; for 14h; Schlenk technique; Inert atmosphere; Irradiation;35%
2-ethyl-1,3-dithiane
6007-23-4

2-ethyl-1,3-dithiane

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2-[2-(4-t-butylphenyl)acetyl]-2-ethyl-1,3-dithiane
172754-37-9

2-[2-(4-t-butylphenyl)acetyl]-2-ethyl-1,3-dithiane

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane 1.) -20 deg C, 1 h, 2.) -20 to 25 deg C, 17 h;
With n-butyllithium 1.) THF, hexane, -20 deg C, 1 h, 2.) THF, 25 deg C, 17 h.; Yield given. Multistep reaction;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

2,6 difluorobenzonitrile
1897-52-5

2,6 difluorobenzonitrile

(4-tert-Butyl-phenyl)-(2-cyano-3-fluoro-phenyl)-acetic acid methyl ester

(4-tert-Butyl-phenyl)-(2-cyano-3-fluoro-phenyl)-acetic acid methyl ester

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran for 19h; Ambient temperature;
ethyl bromide
74-96-4

ethyl bromide

methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

methyl 2-(4-t-butylphenyl)butanoate
211314-95-3

methyl 2-(4-t-butylphenyl)butanoate

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: ethyl bromide In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

benzyl bromide
100-39-0

benzyl bromide

2-(4-tert-butyl-phenyl)-3-phenyl-propionic acid methyl ester
320342-75-4

2-(4-tert-butyl-phenyl)-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: benzyl bromide In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

propyl bromide
106-94-5

propyl bromide

2-(4-tert-butyl-phenyl)-pentanoic acid methyl ester
320342-73-2

2-(4-tert-butyl-phenyl)-pentanoic acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: propyl bromide In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

2-(4-tert-butyl-phenyl)-4-phenyl-butyric acid methyl ester
320342-77-6

2-(4-tert-butyl-phenyl)-4-phenyl-butyric acid methyl ester

Conditions
ConditionsYield
Stage #1: methyl 2-(4-tert-butylphenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃;
Stage #2: 1-phenyl-2-bromoethane In tetrahydrofuran at -78℃; for 2h; Further stages.;
methyl 2-(4-tert-butylphenyl)acetate
3549-23-3

methyl 2-(4-tert-butylphenyl)acetate

(4-tert-butyl-phenyl)-acetic acid benzyl ester
1046319-72-5

(4-tert-butyl-phenyl)-acetic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / methanol
2: Cs2CO3 / dimethylformamide
View Scheme

3549-23-3Relevant articles and documents

Production method of methyl p-tert-butylphenylacetate

-

Paragraph 0017-0032, (2022/01/08)

The invention discloses a production method of methyl p-tert-butylphenylacetate. The method takes p-tert-butylphenylacetic acid and absolute methanol as initial raw materials, and comprises the following reaction operations: heating and refluxing for esterifying and dehydrating p-tert-butylphenylacetic acid and absolute methanol as raw materials under the catalytic action of trifluoromethanesulfonic acid, after the reaction is completed, distilling excessive methanol, cooling residues to room temperature, washing an organic phase once by using a saturated saline solution, standing for layering, separating a water phase, combining the organic phases, neutralizing the organic phases by using 10% sodium carbonate liquid until the pH value is 7-8, standing for layering, separating the water phase, desolventizing the organic phases to the bottom temperature of 80 DEG C, cooling to obtain a crude product, carrying out reduced pressure rectification, and collecting fractions at 122-124 DEG C/1.2 Kpa to obtain the finished product of the methyl p-tert-butylphenylacetate. The raw materials are easy to obtain and low in price, conditions are easy to control and operate, and the product is low in cost, good in quality and suitable for large-scale production.

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo

supporting information, p. 7758 - 7761 (2021/08/13)

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Palladium-Catalyzed Carbonylative Direct Transformation of Benzyl Amines under Additive-Free Conditions

Li, Yahui,Wang, Zechao,Wu, Xiao-Feng

, p. 738 - 741 (2018/01/17)

In this communication, we developed a new procedure for the direct carbonylative transformation of benzyl amines. Using dimethyl carbonate as the solvent, methyl 2-arylacetates can be produced in good to excellent yields from the corresponding primary, secondary, and tertiary benzyl amines with palladium as the catalyst. Notably, no base or any other additive is required here. In addition, our procedure can also be applied in the preparation of methylphenidate, which is a marketing drug and used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy.

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