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626-86-8 Usage

Chemical Properties

solid

Uses

Adipic acid monoethyl ester is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 1252, 1964 DOI: 10.1021/jo01028a504Synthetic Communications, 9, p. 669, 1979 DOI: 10.1080/00397917908066715

Biochem/physiol Actions

Adipic acid monoethyl ester (AMME) suppresses the spore germination and mycelium development in phytopathogen Botrytis cinerea.AMME has antifungal properties.

Check Digit Verification of cas no

The CAS Registry Mumber 626-86-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 6 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 626-86:
(5*6)+(4*2)+(3*6)+(2*8)+(1*6)=78
78 % 10 = 8
So 626-86-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O4/c1-2-12-8(11)6-4-3-5-7(9)10/h2-6H2,1H3,(H,9,10)

626-86-8 Well-known Company Product Price

  • Brand
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  • Alfa Aesar

  • (B24006)  Adipic acid monoethyl ester, 98%   

  • 626-86-8

  • 5g

  • 347.0CNY

  • Detail
  • Alfa Aesar

  • (B24006)  Adipic acid monoethyl ester, 98%   

  • 626-86-8

  • 25g

  • 775.0CNY

  • Detail

626-86-8SDS

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 Monoethyl Adipate

1.2 Other means of identification

Product number -
Other names 6-ethoxy-6-oxohexanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:626-86-8 SDS

626-86-8Synthetic route

Adipic acid
124-04-9

Adipic acid

ethanol
64-17-5

ethanol

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With acetic acid In chloroform; water at 60℃; for 8h; Reagent/catalyst; Temperature; Solvent;98.4%
With aluminum oxide at 25℃; for 48h; Time; Green chemistry; chemoselective reaction;28%
With sulfuric acid
adipic acid benzyl ethyl ester

adipic acid benzyl ethyl ester

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr; for 1.5h; Inert atmosphere;95%
6-hydroxy-hexanoic acid ethyl ester
5299-60-5

6-hydroxy-hexanoic acid ethyl ester

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With iodosylbenzene; potassium bromide In water at 20℃; for 2h; Oxidation;92%
6-hydroxy-hexanoic acid ethyl ester
5299-60-5

6-hydroxy-hexanoic acid ethyl ester

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

hexanedioic acid 5-ethoxycarbonyl-pentyl ester ethyl ester

hexanedioic acid 5-ethoxycarbonyl-pentyl ester ethyl ester

Conditions
ConditionsYield
With potassium bromide; poly(diacetoxyiodo)styrene In water at 80℃; for 7h;A 92%
B n/a
Adipic acid
124-04-9

Adipic acid

ethyl acetate
141-78-6

ethyl acetate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With iron(III) perchlorate for 2h; Ambient temperature;90%
1-iodo-butane
542-69-8

1-iodo-butane

Hexanedioic acid ethyl ester 6-(2-methoxy-ethyl)-pyridin-2-yl ester
78437-79-3

Hexanedioic acid ethyl ester 6-(2-methoxy-ethyl)-pyridin-2-yl ester

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

6-oxo-decanoic acid ethyl ester
4144-61-0

6-oxo-decanoic acid ethyl ester

Conditions
ConditionsYield
With nickel dichloride; zinc In N,N-dimethyl-formamide at 50℃; for 5h;A 8%
B 86%
ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

carbon dioxide
124-38-9

carbon dioxide

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
Stage #1: ethyl 5-bromovalerate With chloro-trimethyl-silane; iodine; ethylene dibromide; lithium chloride; zinc In tetrahydrofuran at 50℃; Inert atmosphere;
Stage #2: carbon dioxide With [Ni(PCy3)2]2(N2) In tetrahydrofuran; toluene at 0℃; under 760.051 Torr; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water; ethyl acetate; toluene
86%
adipic acid ethyl ester-amide
1190-69-8

adipic acid ethyl ester-amide

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With 4,5,6,7-tetrafluoroisobenzofuran-1,3-dione at 135℃; for 60h;83%
Adipic acid
124-04-9

Adipic acid

Ethyl propionate
105-37-3

Ethyl propionate

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

diethyl adipate
141-28-6

diethyl adipate

Conditions
ConditionsYield
With Dowex 50Wx2 In octane at 70℃; for 4h; Esterification;A 72%
B 7%
ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

carbon dioxide
124-38-9

carbon dioxide

potassium carbonate
584-08-7

potassium carbonate

A

ethyl n-valerate
539-82-2

ethyl n-valerate

B

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; 2.9-dimethyl-1,10-phenanthroline; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C60H36N2 In N,N-dimethyl-formamide at 20℃; for 24h; Molecular sieve; Irradiation;A 25 %Spectr.
B 66%
ethyl 5-bromovalerate
14660-52-7

ethyl 5-bromovalerate

carbon dioxide
124-38-9

carbon dioxide

potassium carbonate
584-08-7

potassium carbonate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; 2.9-dimethyl-1,10-phenanthroline; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C60H36N2 In N,N-dimethyl-formamide at 20℃; for 24h; Molecular sieve; Irradiation;66%
Adipic acid
124-04-9

Adipic acid

ethanol
64-17-5

ethanol

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

diethyl adipate
141-28-6

diethyl adipate

Conditions
ConditionsYield
With Diethyl carbonate at 180℃; under 10343.2 Torr; for 5h; Inert atmosphere;A 65%
B 35%
With tetrachloromethane; sulfuric acid
diethyl adipate
141-28-6

diethyl adipate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 0℃; for 16h;60%
With potassium hydroxide at 25℃;
With potassium hydroxide durch partielle Verseifung;
ethyl 5-cyanovalerate
4450-39-9

ethyl 5-cyanovalerate

A

3,4,5,6-tetrafluorophthalimide
652-11-9

3,4,5,6-tetrafluorophthalimide

B

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With 4,5,6,7-tetrafluoroisobenzofuran-1,3-dione at 135℃; for 96h;A n/a
B 56%
2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With potassium hydroxide; 18-crown-6 ether In ethanol; benzene 1.) room temperature, 2 h, 2.) reflux, 20 h;50%
ethanol
64-17-5

ethanol

cyclohexanone-2-ol
533-60-8

cyclohexanone-2-ol

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

diethyl adipate
141-28-6

diethyl adipate

Conditions
ConditionsYield
With potassium peroxomonosulfate at 20℃; for 18h;A 25%
B 49%
ethanol
64-17-5

ethanol

2-acetylcyclohexanone
874-23-7

2-acetylcyclohexanone

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

diethyl adipate
141-28-6

diethyl adipate

Conditions
ConditionsYield
With potassium peroxomonosulfate at 20℃; for 18h;A 48%
B 35%
ethanol
64-17-5

ethanol

cyclohexane-1,2-dione
765-87-7

cyclohexane-1,2-dione

A

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

B

diethyl adipate
141-28-6

diethyl adipate

Conditions
ConditionsYield
With potassium peroxomonosulfate at 20℃; for 18h;A 28%
B 44%
Adipic acid
124-04-9

Adipic acid

ethanol
64-17-5

ethanol

diethyl adipate
141-28-6

diethyl adipate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With hydrogenchloride; dibutyl ether
Adipic acid
124-04-9

Adipic acid

diethyl adipate
141-28-6

diethyl adipate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

diethyl adipate
141-28-6

diethyl adipate

sodium ethanolate
141-52-6

sodium ethanolate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With ethanol; water
O1-benzoyl-monoperoxyadipic acid-6-ethyl ester
855597-17-0

O1-benzoyl-monoperoxyadipic acid-6-ethyl ester

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

A

N,N,N',N'-tetramethylbenzidine
366-29-0

N,N,N',N'-tetramethylbenzidine

B

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

C

benzoic acid
65-85-0

benzoic acid

D

5-benzoyloxy-valeric acid ethyl ester

5-benzoyloxy-valeric acid ethyl ester

Conditions
ConditionsYield
Pyrolysis;
ethyl 6-chloro-6-oxohexanoate
1071-71-2

ethyl 6-chloro-6-oxohexanoate

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dry ammonia gas
2: 83 percent / tetrafluorophthalic anhydride / 60 h / 135 °C
View Scheme
potassium pyrrole

potassium pyrrole

2-bromohexanedioic acid,6-ethyl ester
3269-62-3

2-bromohexanedioic acid,6-ethyl ester

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
In water; benzene
5-carboethoxypentanal
27983-42-2

5-carboethoxypentanal

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Conditions
ConditionsYield
With air at 21℃; for 2h;
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
103421-61-0

3-amino-1-methyl-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

C24H27N3O4
1449305-59-2

C24H27N3O4

Conditions
ConditionsYield
With benzotriazol-1-ol In chloroform at 20℃; for 18h;98%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

adipic acid ethyl methyl ester
18891-13-9

adipic acid ethyl methyl ester

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;98%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Benzophenone oxime
574-66-3

Benzophenone oxime

ethyl 6-(((diphenylmethylene)amino)oxy)-6-oxohexanoate

ethyl 6-(((diphenylmethylene)amino)oxy)-6-oxohexanoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;98%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

ethyl 6-chloro-6-oxohexanoate
1071-71-2

ethyl 6-chloro-6-oxohexanoate

Conditions
ConditionsYield
With thionyl chloride for 1.5h; Heating;96%
With oxalyl dichloride for 2h; Heating;73%
With thionyl chloride
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

benzyl alcohol
100-51-6

benzyl alcohol

adipic acid benzyl ethyl ester

adipic acid benzyl ethyl ester

Conditions
ConditionsYield
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;96%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

diethyl adipate
141-28-6

diethyl adipate

Conditions
ConditionsYield
microwave irradiation;95%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

dibenzyl dicarbonate
31139-36-3

dibenzyl dicarbonate

adipic acid benzyl ethyl ester

adipic acid benzyl ethyl ester

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;93%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

dimethyl dicarbonate
4525-33-1

dimethyl dicarbonate

adipic acid ethyl methyl ester
18891-13-9

adipic acid ethyl methyl ester

Conditions
ConditionsYield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;91%
thionyl chloride
7719-09-7

thionyl chloride

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

ethyl 6-chloro-6-oxohexanoate
1071-71-2

ethyl 6-chloro-6-oxohexanoate

Conditions
ConditionsYield
89%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

ethanethiol
75-08-1

ethanethiol

S-ethyl O-ethyl adipic acid diester
78647-27-5

S-ethyl O-ethyl adipic acid diester

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Steglich Esterification;89%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Buprenorphine
52485-79-7

Buprenorphine

C37H53NO7*ClH

C37H53NO7*ClH

Conditions
ConditionsYield
Stage #1: adipinic acid monoethyl ester; Buprenorphine With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
Stage #2: With ethanol; acetyl chloride at 0℃; for 2h;
89%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

phenylboronic acid
98-80-6

phenylboronic acid

ethyl 6-oxo-6-phenylhexanoate
4248-25-3

ethyl 6-oxo-6-phenylhexanoate

Conditions
ConditionsYield
With P(p-CH3OC6H4)3; water; dimethyl dicarbonate; palladium diacetate In tetrahydrofuran at 20℃;88%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

(3-amino-5-(3,5-dimethylisoxazol-4-yl)phenyl)(phenyl)methanone

(3-amino-5-(3,5-dimethylisoxazol-4-yl)phenyl)(phenyl)methanone

ethyl 6-((3-benzoyl-5-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-6-oxohexanoate

ethyl 6-((3-benzoyl-5-(3,5-dimethylisoxazol-4-yl)phenyl)amino)-6-oxohexanoate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;87%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

2,2-Diphenylethylamine
3963-62-0

2,2-Diphenylethylamine

5-(2,2-diphenyl-ethylcarbamoyl)-pentanoic acid ethyl ester
573986-16-0

5-(2,2-diphenyl-ethylcarbamoyl)-pentanoic acid ethyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane86%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

(S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride
101403-24-1

(S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride

(S)-ethyl 6-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-6-oxohexanoate
1403822-89-8

(S)-ethyl 6-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-6-oxohexanoate

Conditions
ConditionsYield
Stage #1: adipinic acid monoethyl ester With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride In dichloromethane at 20℃; for 20h; Inert atmosphere;
86%
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

Hexanedioic acid 2,5-dioxo-pyrrolidin-1-yl ester ethyl ester

Hexanedioic acid 2,5-dioxo-pyrrolidin-1-yl ester ethyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 20h; Ambient temperature;85%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

dimedone
126-81-8

dimedone

6-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-6-hydroxy-hexanoic acid ethyl ester
244161-53-3

6-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-6-hydroxy-hexanoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: adipinic acid monoethyl ester With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 0.416667h;
Stage #2: dimedone In N,N-dimethyl-formamide for 48h;
84%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

ethyl 5-(N-methoxy-N-methylcarbamoyl)pentanoate
163559-10-2

ethyl 5-(N-methoxy-N-methylcarbamoyl)pentanoate

Conditions
ConditionsYield
Stage #1: adipinic acid monoethyl ester With trichloroacetonitrile; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
83%
With 2-bromo-1-methyl-pyridinium iodide; triethylamine In dichloromethane for 6h; Heating;82%
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In acetonitrile at 20℃; for 1.5h;82%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

3-chloroindazole
29110-74-5

3-chloroindazole

C14H17ClN2O2

C14H17ClN2O2

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine; bathophenanthroline; iodomesitylene diacetate In 1,4-dioxane at 20℃; for 1h; Inert atmosphere; Irradiation; regioselective reaction;80%
dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

adipic acid ethyl methyl ester
18891-13-9

adipic acid ethyl methyl ester

Conditions
ConditionsYield
With pyridine; copper (II) carbonate hydroxide at 90℃; for 24h; Chan-Lam Coupling;78%
adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

thiosemicarbazide
79-19-6

thiosemicarbazide

ethyl 5-(5-amino-1,3,4-thiadiazol-2-yl)pentanoate

ethyl 5-(5-amino-1,3,4-thiadiazol-2-yl)pentanoate

Conditions
ConditionsYield
With trichlorophosphate for 0.5h; Reflux;77.3%
With trichlorophosphate at 80℃; for 2h;77.3%
With trichlorophosphate at 85℃; for 4h;42%
With trichlorophosphate at 85℃; for 4h;41.85%
6-methyltetrahydropyran-2,4-dione
85825-79-2

6-methyltetrahydropyran-2,4-dione

adipinic acid monoethyl ester
626-86-8

adipinic acid monoethyl ester

3-(5-Ethoxycarbonylpentanoyl)-6-methyltetrahydropyran-2,4-dione

3-(5-Ethoxycarbonylpentanoyl)-6-methyltetrahydropyran-2,4-dione

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane for 8h; Acylation;77%

626-86-8Relevant articles and documents

Oxidation of cyclohexanone and/or cyclohexanol catalyzed by Dawson-type polyoxometalates using hydrogen peroxide

Dermeche, Leila,Idrissou, Yasmina,Mazari, Tassadit,Moudjahed, Mohammed,Rabia, Cherifa

, (2022/03/07)

The oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture using as catalyst, Dawson-type polyoxometalates (POMs) of formula, α- and β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 and hydrogen peroxide, carried out at 90 °C with a reaction time of 20 h, led to a high number of mono- and di-acids which were identified by GC-MS. Levulinic, 6-hydroxyhexanoic, adipic, glutaric and succinic acids, major products were evaluated by HPLC. Regardless of the substrate nature, all POMs exhibited high catalytic activity with 94–99% of conversion, whereas the formation of the different products is sensitively related to both the composition and symmetry of the POMs and the substrate nature. The main products are adipic acid in the presence of α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62, levulinic acid in the presence of α1-K7P2Mo5VW12O62 and β-K6P2W18O62 and 6-hydroxyhexanoic acid in the presence of α- and β-K6P2W18O62. Graphical abstract: High catalytic activity was observed with?α- and?β-K6P2W18O62, α-K6P2Mo6W12O62 and α1-K7P2Mo5VW12O62 Dawson-type for the oxidation of cyclohexanone, cyclohexanol or cyclohexanone/cyclohexanol mixture, in the hydrogen peroxide presence, to several oxygenated products. Adipic, levulinic and 6-hydroxyhexanoic acids are the main products. The peroxo- species formed in situ could be the active sites.[Figure not available: see fulltext.]

Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis

Meng, Qing-Yuan,Wang, Shun,K?nig, Burkhard

supporting information, p. 13426 - 13430 (2017/10/07)

We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.

Selective monomethyl esterification of linear dicarboxylic acids with bifunctional alumina catalysts

Santacroce, Veronica,Bigi, Franca,Casnati, Alessandra,Maggi, Raimondo,Storaro, Loretta,Moretti, Elisa,Vaccaro, Luigi,Maestri, Giovanni

supporting information, p. 5764 - 5768 (2016/11/06)

An environmentally friendly protocol for the selective protection of dicarboxylic acids is reported using methanol as a cheap esterifying agent and alumina as a heterogeneous catalyst; the selectivity of the process has been ascribed to a balanced acidity/basicity of the bifunctional alumina catalyst.

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