Conditions | Yield |
---|---|
Stage #1: Glyoxilic acid In water at 70℃; under 37.5038 Torr; Stage #2: ethanol; sulfuric acid In water Product distribution / selectivity; Heating / reflux; | 90% |
at 120℃; | |
With hydrogenchloride unter Entfernen von Wasser; | |
In water; benzene Heating; |
Conditions | Yield |
---|---|
sulfuric acid Product distribution / selectivity; Heating / reflux; | 90% |
Conditions | Yield |
---|---|
With hydrogenchloride at 0 - 5℃; | 85% |
ethanol
3,6-diethoxy-2,5-piperazinedione
A
ethyl 2-(diethoxyacetylamino)-2-ethoxyacetate
B
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With hydrogen bromide for 1.5h; Product distribution; Heating; | A 42% B 31% |
ethanol
ethyl 2-(diethoxyacetylamino)-2-ethoxyacetate
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With hydrogenchloride for 3h; Heating; | 39% |
With hydrogenchloride In ethanol for 3h; Product distribution; Heating; | 39% |
ethanol
ethyl N-(2-diethoxyacetyl)glycinate
A
glycine ethyl ester hydrochloride
B
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With hydrogenchloride for 3h; Heating; | A 35% B 38% |
With hydrogenchloride for 3h; Product distribution; Heating; | A 35% B 38% |
diethoxycarbonium fluoroborate
A
pentaethoxyethane
B
ethyl 2,2,3,3-tetraethoxypropanoate
C
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; | A 11% B 35% C 2% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; | A 11% B 35% C 2% |
ethanol
3,6-Dibromo-piperazine-2,5-dione
A
ethyl N-(2-diethoxyacetyl)glycinate
B
3,6-diethoxy-2,5-piperazinedione
C
N-(1-ethoxy-1-ethoxycarbonylmethyl)oxamide
D
ethyl 2-(diethoxyacetylamino)-2-ethoxyacetate
E
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; other nucleophiles and reactions products; | A 13% B 3.3% C 1.6% D 24.8% E 4.2% |
Conditions | Yield |
---|---|
Veresterung mit alkoh. Schwefelsaeure; | |
Veresterung mit alkoh. Salzsaeure; | |
Behandlung des Silbersalzes mit Aethyljodid; | |
folgende Veresterung mit alkoh. HCl; |
dichloro-acetic acid
sodium ethanolate
A
ethyl 2-ethoxyglycolate
B
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
und Veresterung des Reaktionsproduktes; |
ethanol
ethyl 2,2-diethoxyethanimidate
A
2,2-diethoxyacetonitrile
B
diethoxyacetamide
C
pentaethoxyethane
D
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With ethanol |
sodium ethanolate
ethyl 1,1-dichloroacetate
A
2,2-diethoxy-3-chloro-succinic acid diethyl ester
B
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With tert-butylhypochlorite |
Conditions | Yield |
---|---|
(i) Mor, (ii) /BRN= 1718733/, HCl; Multistep reaction; |
Conditions | Yield |
---|---|
With pyridine; triethylamine In benzene |
ethanol
ethyl 2-bromo-2-ethoxy-acetate
A
2-Ethoxy-3-ethoxycarbonyl-bernsteinsaeurediethylester
B
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With sodium 1.) RT; 2.) 70 deg C, 3 h; Yield given. Multistep reaction; |
ethanol
3,6-Dibromo-piperazine-2,5-dione
A
ethyl N-(2-diethoxyacetyl)glycinate
B
3,6-diethoxy-2,5-piperazinedione
C
ethyl 2-(diethoxyacetylamino)-2-ethoxyacetate
D
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; Yield given. Further byproducts given. Yields of byproduct given; |
ethanol
Glyoxilic acid
A
3,6-Diethoxy-[1,4]dioxane-2,5-dione
B
diethoxy-4,5-dioxolanne-1,3 carboxylate-2 d'ethyle
C
Ethoxy-(ethoxy-ethoxycarbonyl-methoxy)-acetic acid ethyl ester
D
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid 1.) benzene, reflux, 3 h; 2.) reflux, 16 h; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With pyridine |
Conditions | Yield |
---|---|
at 100 - 130℃; |
Conditions | Yield |
---|---|
With hydrogenchloride |
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With water Electrolysis.an Platin-Elektroden; |
2,3-diethoxy-3-oxopropionic acid
water
A
ethyl 2-ethoxyglycolate
B
ethanol
C
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
das Kaliumsalz liefert an Platin-Elektroden; Pr.5: Acetaldehyd, Pr.6: Formaldehyd, Pr.7: Oxalsaeure.Electrolysis; |
Ethyl diethoxyacetate
ethyl 2-chloro-2-ethoxyacetate
Conditions | Yield |
---|---|
With iodine; acetyl chloride at 50℃; for 22h; | 100% |
With iodine; acetyl chloride at 50℃; for 24h; Product distribution / selectivity; | 100% |
With acetyl chloride; iodine at 50℃; for 1h; | 82% |
With phosphorus pentachloride at 80 - 140℃; | |
With iodine; acetyl chloride |
Ethyl diethoxyacetate
diethoxyacetamide
Conditions | Yield |
---|---|
With ammonia In ethanol for 48h; Ambient temperature; | 100% |
With ammonia; water for 40h; | 99% |
With ammonium hydroxide at 25 - 30℃; | 95% |
Conditions | Yield |
---|---|
With titanium(IV) iodide In acetonitrile at -78℃; | 100% |
Conditions | Yield |
---|---|
With iodine | 100% |
Ethyl propionate
Ethyl diethoxyacetate
ethyl 4,4-diethoxy-2-methyl-3-oxobutanoate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; Claisen condensation; | 99% |
With sodium at 80℃; | |
With sodium ethanolate |
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane; toluene at 20℃; for 96h; Inert atmosphere; | 99% |
(trimethylsilyl)methylmagnesium chloride
Ethyl diethoxyacetate
1,1-Diethoxy-3-trimethylsilanyl-2-trimethylsilanylmethyl-propan-2-ol
Conditions | Yield |
---|---|
With cerium(III) chloride | 98% |
With cerium(III) chloride In tetrahydrofuran at -78℃; | 90% |
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 5h; Heating; | 97% |
benzylmagnesium chloride
Ethyl diethoxyacetate
1,1-diethoxy-3-phenylpropane-2-one
Conditions | Yield |
---|---|
In tetrahydrofuran at -78℃; for 2h; | 96% |
In tetrahydrofuran at -78℃; for 12h; | 93% |
In tetrahydrofuran at -78℃; for 2h; | 91.8% |
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 100℃; for 6h; | 96% |
p-toluamidoxime
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 100℃; for 6h; | 96% |
Ethyl diethoxyacetate
2,2-diethoxy acetic acid
Conditions | Yield |
---|---|
With water; sodium hydroxide at 70℃; for 0.5h; Industrial scale; | 95.1% |
Stage #1: Ethyl diethoxyacetate With water; sodium hydroxide In ethanol at 20℃; for 1h; Stage #2: With hydrogenchloride In water | 88% |
With sodium hydroxide In ethanol at 20℃; for 3h; | 85% |
dimethyl amine
Ethyl diethoxyacetate
2,2-diethoxy-N,N-dimethylacetamide
Conditions | Yield |
---|---|
With sodium methylate In methanol at 45 - 50℃; for 4h; Product distribution / selectivity; | 95% |
With calcium chloride at 15 - 100℃; | |
With n-butyllithium; hexane 1.) -78 deg C, 15 min, THF, 2.) 3 h, from -78 deg C to room temperature; 1 h, room temperature; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With titanium tetrachloride In nitromethane at 20℃; for 12h; Cooling with ice; | 95% |
1.3-propanedithiol
Ethyl diethoxyacetate
ethyl 1,3-dithiane-2-carboxylate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In chloroform for 1.5h; Heating / reflux; | 94% |
With boron trifluoride diethyl etherate In dichloromethane for 14h; Ambient temperature; | 60% |
Stage #1: 1.3-propanedithiol With boron trifluoride diethyl etherate In chloroform at -70℃; Stage #2: Ethyl diethoxyacetate In chloroform at 70℃; for 1h; | 47% |
N'-hydroxy-3-methylbenzimidamide
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 100℃; for 6h; | 94% |
Conditions | Yield |
---|---|
Stage #1: ethyl acetate; Ethyl diethoxyacetate With sodium at 20 - 60℃; for 20h; Inert atmosphere; Stage #2: With hydrogenchloride In ethanol; water pH=6; | 93% |
With sodium at 20 - 60℃; for 19h; Claisen Condensation; Inert atmosphere; | 89% |
With sodium hydride In tetrahydrofuran at 20℃; for 20.5h; Heating / reflux; | 81% |
Conditions | Yield |
---|---|
Stage #1: chloro-trimethyl-silane; C17H24N2O5 In 1,2-dichloro-ethane at 20℃; for 2h; Reflux; Stage #2: Ethyl diethoxyacetate With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 16h; stereoselective reaction; | 93% |
2-bromo-5-fluoropyridine
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h; | 92% |
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; | 92% |
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h; | 92% |
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h; | 92% |
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 100℃; for 6h; | 92% |
4-fluoro-benzamidoxime
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 100℃; for 6h; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 0℃; for 48h; | 91% |
Ethyl diethoxyacetate
2,2-dihydroxyacetic acid
glyoxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: Ethyl diethoxyacetate; 2,2-dihydroxyacetic acid With toluene-4-sulfonic acid at 90℃; for 27h; Stage #2: With phosphorus pentoxide at 90 - 100℃; for 2h; | 90% |
3-bromo-N'-hydroxybenzenecarboximidamide
Ethyl diethoxyacetate
Conditions | Yield |
---|---|
With potassium carbonate In neat (no solvent) at 100℃; for 6h; | 90% |
4-methoxy-N-[(E)-phenylmethylidene]aniline
Ethyl diethoxyacetate
3,3-diethoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane at -70 - 20℃; for 19.5h; Cycloaddition; | 89% |
phenylmagnesium bromide
Ethyl diethoxyacetate
hydroxy-diphenyl-acetaldehyde
Conditions | Yield |
---|---|
Stage #1: phenylmagnesium bromide; Ethyl diethoxyacetate In tetrahydrofuran at 20 - 90℃; for 0.666667h; Inert atmosphere; Stage #2: With hydrogenchloride In water; acetone at 70℃; for 1h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In dimethoxyethane, 1,2; ethanol at 50℃; for 7h; Heating / reflux; | 88.7% |
[4-(benzylideneamino)phenyl]methanol
Ethyl diethoxyacetate
3,3-diethoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide for 12h; Ambient temperature; | 88% |
Product Name: Ethyl diethoxyacetate (CAS NO.6065-82-3)
Molecular Formula: C8H16O4
Molecular Weight: 176.21g/mol
Mol File: 6065-82-3.mol
EINECS: 227-999-8
Melting Point: 198-200
Boiling point: 199 °C at 760 mmHg
Flash Point: 73.3 °C
Density: 0.994 g/cm3
Refractive index: n20/D 1.410(lit.)
Surface Tension: 29.2 dyne/cm
Enthalpy of Vaporization: 43.52 kJ/mol
Vapour Pressure: 0.349 mmHg at 25°C
XLogP3-AA: 1.1
H-Bond Donor: 0
H-Bond Acceptor: 4
Structure Descriptors of Ethyl diethoxyacetate (CAS NO.6065-82-3):
IUPAC Name: ethyl 2,2-diethoxyacetate
Canonical SMILES: CCOC(C(=O)OCC)OCC
InChI: InChI=1S/C8H16O4/c1-4-10-7(9)8(11-5-2)12-6-3/h8H,4-6H2,1-3H3
InChIKey: XCLBIKIQSCTANZ-UHFFFAOYSA-N
Product Categories: Pharmaceutical Intermediates; All Aliphatics; Aliphatics; Miscellaneous Reagents
Safety Information of Ethyl diethoxyacetate (CAS NO.6065-82-3):
Hazard Codes: Xi
Safety Statements: 24/25-36/37-26
24: Avoid contact with skin
25: Avoid contact with eyes
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
RIDADR: 2810
WGK Germany: 2
Hazard Note: Irritant
HS Code: 29189090
Ethyl diethoxyacetate , its CAS NO. is 6065-82-3, the synonyms are EINECS 227-999-8 ; Acetic acid, 2,2-diethoxy-, ethyl ester ; Acetic acid, diethoxy-, ethyl ester .
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