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99469-99-5

Basic Information
CAS No.: 99469-99-5
Name: 4-Ethoxycarbonyl-3-ethoxyphenyla-cetic acid
Article Data: 9
Cas Database
Molecular Structure:
Molecular Structure of 99469-99-5 (4-Ethoxycarbonyl-3-ethoxyphenyla-cetic acid)
Formula: C13H16O5
Molecular Weight: 252.267
Synonyms: 3-Ethoxy-4-(ethoxycarbonyl)benzeneaceticacid;Ethyl 4-carboxymethyl-2-ethoxybenzoate;[3-Ethoxy-4-(ethoxycarbonyl)phenyl]aceticacid;3-Ethoxy-4-ethoxycarbonylphenyl acetic acid;
EINECS: 427-630-2
Density: 1.191 g/cm3
Melting Point: 78-80 °C
Boiling Point: 414.816 °C at 760 mmHg
Flash Point: 155.936 °C
Solubility: N/A
Appearance: white to pale yellow solid
Hazard Symbols: IrritantXi
Risk Codes: 41
Safety: 26-39
Transport Information: N/A
PSA: 72.83000
LogP: 1.88910
Synthetic route
332347-69-0

ethyl 2-ethoxy-4-(2-ethoxy-2-oxoethyl)benzoate

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water pH=3; Large scale;90.5%
Stage #1: ethyl 2-ethoxy-4-ethoxycarbonylmethyl-benzoate With sodium hydroxide; water In methanol at 10 - 15℃; for 1 - 2h;
Stage #2: With hydrogenchloride In water at 0 - 5℃; pH=3 - 4;
77.8%
With sodium hydroxide In ethanol at 23 - 25℃; for 1.5h;59%
With water; sodium hydroxide In ethanol at 30℃; for 1h;
88709-18-6

2-ethoxy-4-methylbenzoic acid

616-38-6

carbonic acid dimethyl ester

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran at -80 - -70℃; for 4h; Temperature;86.2%

C16H22O5

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water pH=3;78.1%

C17H24O5

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
With hydrogenchloride In water pH=3;77.7%
124-38-9

carbon dioxide

88709-17-5

ethyl 2-ethoxy-4-methyl-benzoate

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -30℃; for 0.5h;
Stage #2: ethyl 2-ethoxy-4-methyl-benzoate With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -75℃; for 2h;
Stage #3: carbon dioxide In tetrahydrofuran; hexane at -75 - 10℃; for 0.5h;
72.7%
Stage #1: ethyl 2-ethoxy-4-methyl-benzoate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -75℃; Inert atmosphere; Industrial scale;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -75℃; Industrial scale;
67%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -30℃; for 0.5h;
Stage #2: ethyl 2-ethoxy-4-methyl-benzoate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane at -75℃; for 2h;
Stage #3: carbon dioxide In tetrahydrofuran; hexane at -75 - 20℃;
59.5%
Stage #1: ethyl 2-ethoxy-4-methyl-benzoate With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 10℃;
23%

ethyl 2-ethoxy-5-(2-oxo-2-(quinolin-8-ylamino)ethyl)benzoate

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
Stage #1: ethyl 2-ethoxy-5-(2-oxo-2-(quinolin-8-ylamino)ethyl)benzoate With ozone In dichloromethane at -78℃; Inert atmosphere;
Stage #2: With copper dichloride In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Microwave irradiation;
42%

ethyl 4-(2-amino-2-oxoethyl)-2-ethoxybenzoate

A

220438-80-2

2-ethoxy-[4-(carboxymethyl)]benzoic acid

B

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at 35℃; for 2h;A n/a
B 39%
50-85-1

2-hydroxy-p-toluic acid

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: K2CO3 / diethyl ether / 30 h / 150 °C
2: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
3: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
4: HCl / Heating
5: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
View Scheme
Multi-step reaction with 5 steps
1: K2CO3 / diethyl ether / 30 h / 150 °C
2: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
3: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
4: aq. HCl / 1.5 h / 20 - 23 °C
5: 39 percent / aq. NaNO2, aq. HCl / 2 h / 35 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / dimethyl sulfoxide / 10.5 h / 40 °C
2.1: diisopropylamine; n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
2.2: -78 - 10 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / dimethyl sulfoxide / 11 h / 40 °C
2.1: diisopropylamine; n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
2.2: -78 - 10 °C
View Scheme
88709-17-5

ethyl 2-ethoxy-4-methyl-benzoate

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
2: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
3: HCl / Heating
4: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
View Scheme
Multi-step reaction with 4 steps
1: N-bromosuccinimide, 2,2'-azo-bis-(isobutyronitril) / CCl4
2: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
3: aq. HCl / 1.5 h / 20 - 23 °C
4: 39 percent / aq. NaNO2, aq. HCl / 2 h / 35 °C
View Scheme
Multi-step reaction with 2 steps
1: dihydrogen peroxide; copper dichloride; bis(diphenylphosphino)ethylamine / tetrahydrofuran / 10 h / 15001.5 Torr / Reflux
2: hydrogenchloride / water / pH 3
View Scheme
Multi-step reaction with 2 steps
1: tert.-butylhydroperoxide; palladium dichloride; depe / tetrahydrofuran / 20 h / 15001.5 Torr / Reflux
2: hydrogenchloride / water / pH 3 / Large scale
View Scheme
110017-07-7

ethyl 4-bromomethyl-2-ethoxy-benzoate

99469-99-5

2-(3-ethoxy-4-(ethoxycarbonyl)phenyl) acetic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
2: HCl / Heating
3: 59 percent / NaOH / ethanol / 1.5 h / 23 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / aq. N-benzyl-tri-n-butylammonium-chloride / CH2Cl2 / 43 h / 20 °C
2: aq. HCl / 1.5 h / 20 - 23 °C
3: 39 percent / aq. NaNO2, aq. HCl / 2 h / 35 °C
View Scheme
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Chemistry

Product Name: 4-Ethoxycarbonyl-3-ethoxyphenyla-cetic acid (CAS NO.99469-99-5)

IUPAC Name: 3-Ethoxy-4-ethoxycarbonyl phenylacetic acid
Molecular Formula: C13H16O5
Molecular Weight: 252.26
Appearance: white to pale yellow solid
Density: 1.191
Melting Point: 78-80 °C
Boiling Point: 414.8 °C at760mmHg
Flash Point: 155.9 °C
Surface Tension:  44.42 dyne/cm 
Enthalpy of Vaporization:  70.41 kJ/mol 
Index of Refraction: 1.527 
Molar Refractivity: 65.084 cm3 
Molar Volume: 211.785 cm3
Categories: Pharmaceutical material and intermeidates; Aromatic Phenylacetic Acids and Derivatives; Aromatics

Uses

 4-Ethoxycarbonyl-3-ethoxyphenyla-cetic acid (CAS NO.99469-99-5) is used as an intermediate for the synthesis of Repaglinide.

Safety Profile

Safety Information of 4-Ethoxycarbonyl-3-ethoxyphenyla-cetic acid (CAS NO.99469-99-5):
Hazard Codes:Xi

Specification

 4-Ethoxycarbonyl-3-ethoxyphenyla-cetic acid , its CAS NO. is 99469-99-5, the synonyms are 3-Ethoxy-4-(ethoxycarbonyl)benzeneacetic acid ; 2-[(4-Ethoxycarbonyl)-3-ethoxyphenyl] acetic acid .