999-10-0

Basic information

• Product Name: Ethyl 4-hydroxybutanoate
• Synonyms: ethylhydroxybutanoate,ethyl4-hydroxybutanoate;4-Hydroxybutanoic acid ethyl ester;Ethyl 4-hydroxybutanoate;Ethyl 4-hydroxybutyrate;4-Hydroxybutyric acid ethyl ester;Butanoic acid, 4-hydroxy-, ethyl ester
• CAS NO: 999-10-0
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• Mol File: 999-10-0.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 205 °C
• Flash Point: 81 °C
• Appearance: /
• Density: 1.027
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Sparingly), Methaol (Slightly)
• PKA: 14.88±0.10(Predicted)
• CAS DataBase Reference: Ethyl 4-hydroxybutanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-hydroxybutanoate(999-10-0)
• EPA Substance Registry System: Ethyl 4-hydroxybutanoate(999-10-0)

Safety Data

• Hazardous Substances Data: 999-10-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 485, 1966 DOI: 10.1021/jo01340a031

InChI:InChI=1/C6H12O3/c1-2-5(3-4-7)6(8)9/h5,7H,2-4H2,1H3,(H,8,9)/p-1

Synthetic route

4-butanolide (96-48-0) + ethanol (64-17-5) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With amberlyst-15 for 20h;	94%
With sulfuric acid Ambient temperature;	80%
With sulfuric acid at 20℃; for 33h;	55%

4-isopropoxycarbonyloxy-butyric acid ethyl ester → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With aluminium trichloride In nitromethane at 25℃; for 3h;	86%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → 4-butanolide (96-48-0) + 5-Hydroxy-2-pentanone (1071-73-4) + ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2)

Conditions	Yield
With sodium hydroxide In ethanol; water at 200℃; for 2h;	A 75% B 5% C 8% D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h;	A 75% B 3% C 8% D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h; Product distribution; other reagent/educt ratio,;	A 15% B 16% C 4% D 62%
With sodium hydroxide In ethanol; water at 200℃; for 2h;	A 15% B 16% C 4% D 62%

4-bromoethylbutanoate (2969-81-5) → ethyl 4-hydroxybutanoate (999-10-0) + ethyl cyclopropylcarboxylate (4606-07-9)

Conditions	Yield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;	A 10% B 68%

4-butanolide (96-48-0) + ethyl acetate (141-78-6) → ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2) + ethyl 2-acetyl-4-acetoxybutyrate (87418-30-2)

Conditions	Yield
With sodium ethanolate at -50℃;	A 9% B 57% C 25%

diethyl 2-ketoglutarate (5965-53-7) → (–)-(S)-diethyl 2-hydroxyglutarate (55094-99-0) + ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With baker's yeast Ambient temperature;	A 18% B 34%

4-butanolide (96-48-0) + triethyloxonium fluoroborate (368-39-8) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 3598090/, MeCN; Multistep reaction;

3,3-Bis-ethylsulfanylcarbonyl-propionic acid ethyl ester (72291-79-3) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
nickel

4-butanolide (96-48-0) + sodium ethanolate (141-52-6) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 5-Hydroxy-2-pentanone (1071-73-4) + ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2) + ethyl acetoacetate (141-97-9) + α-(2-Tetrahydrofuranylidene)-γ-butyrolactone (65652-24-6)

Conditions	Yield
at 100℃; under 1064 Torr; for 0.5h; Product distribution; various molar ratio of the reagents, other temp., other pressure, other time;

...Expand

4-bromoethylbutanoate (2969-81-5) → 4-butanolide (96-48-0) + ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With water; triethylamine In ethanol at 120.1℃; Kinetics; further temperatures, further solvent, activation enthalpy and entropy;

ethyl 4-oxobutanoate (10138-10-0) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With glycerol dehydrogenase; 2-propanol-NAD(1+) potassium phosphate buffer, pH 7;

4-butanolide (96-48-0) + ethanol (64-17-5) + sulfuric acid (7664-93-9) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
bei Raumtemperatur;

succinic acid diethyl ester (123-25-1) + copper-chromium oxide → 4-butanolide (96-48-0) + Butane-1,4-diol (110-63-4) + ethyl 4-hydroxybutanoate (999-10-0) + butyric acid (107-92-6)

Conditions	Yield
at 250℃; under 220652 Torr; Produkt 5: Tetrahydrofuran(?).Hydrogenation;
at 250℃; under 220652 Torr; Produkt 5: Tetrahydrofuran(?).Hydrogenation;

hydrochloride of γ-amino-butyric acid ethyl ester → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With sodium nitrite

ethyl γ-aminobutyrate hydrochloride (6937-16-2) + NaNO2 → ethyl 4-hydroxybutanoate (999-10-0)

ethanol (64-17-5) + thiosuccinic acid O-ethyl ester-S-benzyl ester (108881-52-3) + Raney nickel → ethyl 4-hydroxybutanoate (999-10-0)

4-ethoxybut-3-ynyloxy-tert-butyl-diphenylsilane (112793-76-7) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
Acid hydrolysis;

1-ethoxy-1-butyn-4-ol (19985-85-4) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 553 mg / imidazole / CH2Cl2 / 1.5 h 2: Acid hydrolysis View Scheme

2-ethoxytetrahydrofuran (13436-46-9) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With ozone for 8h; Ionic liquid;

4-butanolide (96-48-0) + ethanol (64-17-5) + sodium ethanolate (141-52-6) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
at 20℃; for 48h;

4-butanolide (96-48-0) + ethanol (64-17-5) → Butane-1,4-diol (110-63-4) + ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With hydrogen at 100℃; under 25502.6 Torr; for 24h; Reagent/catalyst; Solvent; Autoclave;

ethyl 4-hydroxybutanoate (999-10-0) + ortho-cresol (95-48-7) → 4-o-tolyloxybutyric acid ethyl ester (56359-11-6)

Conditions	Yield
With Si-Al supported catalyst at 90℃; for 1h;	97.7%

ethyl 4-hydroxybutanoate (999-10-0) + 4-{[(1R,2S)-2-methylcyclopentyl]amino}-2-(methylsulfanyl)pyrimidine-5-carbaldehyde → 6-(2-hydroxyethyl)-8-[(1R,2S)-2-methylcyclopentyl]-2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Conditions	Yield
Stage #1: ethyl 4-hydroxybutanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: 4-{[(1R,2S)-2-methylcyclopentyl]amino}-2-(methylsulfanyl)pyrimidine-5-carbaldehyde In tetrahydrofuran at 20℃; for 18h;	95%

ethyl 4-hydroxybutanoate (999-10-0) + p-toluenesulfonyl chloride (98-59-9) → 4-(p-toluenesulfonyloxy)butyric acid ethyl ester

Conditions	Yield
With triethylamine In dichloromethane at 5 - 20℃; for 6h;	92%
With triethylamine In diethyl ether at 0℃; for 2h;	72%
With triethylamine at 0℃; for 2h;
With dmap; triethylamine In dichloromethane

ethyl 4-hydroxybutanoate (999-10-0) + benzylamine (100-46-9) → N-benzyl-4-hydroxybutanamide (19340-88-6)

Conditions	Yield
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;	90%

diazoacetic acid ethyl ester (623-73-4) + ethyl 4-hydroxybutanoate (999-10-0) → 4-ethoxycarbonylmethoxy-butyric acid ethyl ester (388109-23-7)

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 20℃; for 73.5h;	87%
rhodium(II) acetate In dichloromethane at 20℃; for 73.5h;	87%

ethyl 4-hydroxybutanoate (999-10-0) → 4-phosphonooxy-butyric acid ethyl ester (98275-36-6)

Conditions	Yield
With PPA

4-butanolide (96-48-0) + ethanol (64-17-5) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With amberlyst-15 for 20h;	94%
With sulfuric acid Ambient temperature;	80%
With sulfuric acid at 20℃; for 33h;	55%

4-isopropoxycarbonyloxy-butyric acid ethyl ester → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With aluminium trichloride In nitromethane at 25℃; for 3h;	86%

3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) → 4-butanolide (96-48-0) + 5-Hydroxy-2-pentanone (1071-73-4) + ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2)

Conditions	Yield
With sodium hydroxide In ethanol; water at 200℃; for 2h;	A 75% B 5% C 8% D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h;	A 75% B 3% C 8% D 12%
With sodium hydroxide In ethanol; water at 200℃; for 2h; Product distribution; other reagent/educt ratio,;	A 15% B 16% C 4% D 62%
With sodium hydroxide In ethanol; water at 200℃; for 2h;	A 15% B 16% C 4% D 62%

4-bromoethylbutanoate (2969-81-5) → ethyl 4-hydroxybutanoate (999-10-0) + ethyl cyclopropylcarboxylate (4606-07-9)

Conditions	Yield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;	A 10% B 68%

4-butanolide (96-48-0) + ethyl acetate (141-78-6) → ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2) + ethyl 2-acetyl-4-acetoxybutyrate (87418-30-2)

Conditions	Yield
With sodium ethanolate at -50℃;	A 9% B 57% C 25%

diethyl 2-ketoglutarate (5965-53-7) → (–)-(S)-diethyl 2-hydroxyglutarate (55094-99-0) + ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With baker's yeast Ambient temperature;	A 18% B 34%

4-butanolide (96-48-0) + triethyloxonium fluoroborate (368-39-8) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
(i) aq. NaOH, (ii) /BRN= 3598090/, MeCN; Multistep reaction;

3,3-Bis-ethylsulfanylcarbonyl-propionic acid ethyl ester (72291-79-3) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
nickel

4-butanolide (96-48-0) + sodium ethanolate (141-52-6) + ethyl acetate (141-78-6) → 3-acetyl-2-oxo-4,5-dihydrofuran (517-23-7) + 5-Hydroxy-2-pentanone (1071-73-4) + ethyl 4-hydroxybutanoate (999-10-0) + ethyl 4-(acetyloxy)butanoate (25560-91-2) + ethyl acetoacetate (141-97-9) + α-(2-Tetrahydrofuranylidene)-γ-butyrolactone (65652-24-6)

Conditions	Yield
at 100℃; under 1064 Torr; for 0.5h; Product distribution; various molar ratio of the reagents, other temp., other pressure, other time;

...Expand

4-bromoethylbutanoate (2969-81-5) → 4-butanolide (96-48-0) + ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With water; triethylamine In ethanol at 120.1℃; Kinetics; further temperatures, further solvent, activation enthalpy and entropy;

ethyl 4-oxobutanoate (10138-10-0) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With glycerol dehydrogenase; 2-propanol-NAD(1+) potassium phosphate buffer, pH 7;

4-butanolide (96-48-0) + ethanol (64-17-5) + sulfuric acid (7664-93-9) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
bei Raumtemperatur;

succinic acid diethyl ester (123-25-1) + copper-chromium oxide → 4-butanolide (96-48-0) + Butane-1,4-diol (110-63-4) + ethyl 4-hydroxybutanoate (999-10-0) + butyric acid (107-92-6)

Conditions	Yield
at 250℃; under 220652 Torr; Produkt 5: Tetrahydrofuran(?).Hydrogenation;
at 250℃; under 220652 Torr; Produkt 5: Tetrahydrofuran(?).Hydrogenation;

hydrochloride of γ-amino-butyric acid ethyl ester → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With sodium nitrite

ethyl γ-aminobutyrate hydrochloride (6937-16-2) + NaNO2 → ethyl 4-hydroxybutanoate (999-10-0)

ethanol (64-17-5) + thiosuccinic acid O-ethyl ester-S-benzyl ester (108881-52-3) + Raney nickel → ethyl 4-hydroxybutanoate (999-10-0)

4-ethoxybut-3-ynyloxy-tert-butyl-diphenylsilane (112793-76-7) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
Acid hydrolysis;

1-ethoxy-1-butyn-4-ol (19985-85-4) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 553 mg / imidazole / CH2Cl2 / 1.5 h 2: Acid hydrolysis View Scheme

2-ethoxytetrahydrofuran (13436-46-9) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With ozone for 8h; Ionic liquid;

4-butanolide (96-48-0) + ethanol (64-17-5) + sodium ethanolate (141-52-6) → ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
at 20℃; for 48h;

4-butanolide (96-48-0) + ethanol (64-17-5) → Butane-1,4-diol (110-63-4) + ethyl 4-hydroxybutanoate (999-10-0)

Conditions	Yield
With hydrogen at 100℃; under 25502.6 Torr; for 24h; Reagent/catalyst; Solvent; Autoclave;

ethyl 4-hydroxybutanoate (999-10-0) + ortho-cresol (95-48-7) → 4-o-tolyloxybutyric acid ethyl ester (56359-11-6)

Conditions	Yield
With Si-Al supported catalyst at 90℃; for 1h;	97.7%

ethyl 4-hydroxybutanoate (999-10-0) + 4-{[(1R,2S)-2-methylcyclopentyl]amino}-2-(methylsulfanyl)pyrimidine-5-carbaldehyde → 6-(2-hydroxyethyl)-8-[(1R,2S)-2-methylcyclopentyl]-2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Conditions	Yield
Stage #1: ethyl 4-hydroxybutanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: 4-{[(1R,2S)-2-methylcyclopentyl]amino}-2-(methylsulfanyl)pyrimidine-5-carbaldehyde In tetrahydrofuran at 20℃; for 18h;	95%

ethyl 4-hydroxybutanoate (999-10-0) + p-toluenesulfonyl chloride (98-59-9) → 4-(p-toluenesulfonyloxy)butyric acid ethyl ester

Conditions	Yield
With triethylamine In dichloromethane at 5 - 20℃; for 6h;	92%
With triethylamine In diethyl ether at 0℃; for 2h;	72%
With triethylamine at 0℃; for 2h;
With dmap; triethylamine In dichloromethane

ethyl 4-hydroxybutanoate (999-10-0) + benzylamine (100-46-9) → N-benzyl-4-hydroxybutanamide (19340-88-6)

Conditions	Yield
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 100℃; for 0.5h; Microwave irradiation;	90%

diazoacetic acid ethyl ester (623-73-4) + ethyl 4-hydroxybutanoate (999-10-0) → 4-ethoxycarbonylmethoxy-butyric acid ethyl ester (388109-23-7)

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 20℃; for 73.5h;	87%
rhodium(II) acetate In dichloromethane at 20℃; for 73.5h;	87%

ethyl 4-hydroxybutanoate (999-10-0) + N-(4-methoxybenzyl)-2,2,2-trichloroacetamide (123558-64-5) → ethyl 4-((4-metoxybenzyl)oxy)butanoate

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane; cyclohexane	86%

ethyl 4-hydroxybutanoate (999-10-0) + tert-butyldimethylsilyl chloride (18162-48-6) → ethyl 4-(t-butyldimethylsiloxy)butanoate (506417-45-4)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃;	85%

ethyl 4-hydroxybutanoate (999-10-0) → ethyl 4-oxobutanoate (10138-10-0)

Conditions	Yield
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 0℃; for 2.16667h; Swern Oxidation; Inert atmosphere;	82%
With sodium acetate; pyridinium chlorochromate In dichloromethane for 2h;	79%
With dipyridinium dichromate In dichloromethane for 48h; Ambient temperature;	63%

ethyl 4-hydroxybutanoate (999-10-0) + 2-monochlorophenol (95-57-8) → ethyl 4-(2-chlorophenoxy)butanoate (111105-19-2)

Conditions	Yield
With ceramic and V-supported catalyst (active component: carrier mass ratio of 10:100) at 110 - 140℃; for 5h;	39.13%

ethyl 4-hydroxybutanoate (999-10-0) → 4-phosphonooxy-butyric acid ethyl ester (98275-36-6)

Conditions	Yield
With PPA

3,4-dihydro-2H-pyran (110-87-2) + ethyl 4-hydroxybutanoate (999-10-0) → 4-(Tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester (117745-48-9)

Conditions	Yield
With hydrogenchloride

ethyl 4-hydroxybutanoate (999-10-0) + 3'-O-methylthiomethyl-5'-pivaloylthymidine → 4-[(2R,3S,4R,5R)-2-(2,2-Dimethyl-propionyloxymethyl)-4-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethoxy]-butyric acid ethyl ester

Conditions	Yield
With N-Bromosuccinimide; lutidine 1.) dichloromethane, 2.) dichloromethane; Yield given. Multistep reaction;

Upstream product

• 123-25-1 succinic acid diethyl ester 
• 96-48-0 4-butanolide 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 13436-46-9 2-ethoxytetrahydrofuran 
• 19985-85-4 1-ethoxy-1-butyn-4-ol 
• 112793-76-7 4-ethoxybut-3-ynyloxy-tert-butyl-diphenylsilane 
• 108881-52-3 thiosuccinic acid O-ethyl ester-S-benzyl ester 
• 6937-16-2 ethyl γ-aminobutyrate hydrochloride 
• 7664-93-9 sulfuric acid 
• 5965-53-7 diethyl 2-ketoglutarate 
• 2969-81-5 Ethyl 4-bromobutyrate 
• 10138-10-0 ethyl 4-oxobutanoate 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 

Downstream Products

• 62557-32-8 ethyl (2-amino-1,3-thiazole-5-yl)acetate 
• 10443-70-6 ethyl 4-(4-chloro-2-methylphenoxy)butyrate 
• 56359-11-6 4-o-tolyloxybutyric acid ethyl ester 
• 111105-19-2 ethyl 4-(2-chlorophenoxy)butanoate 
• 1068522-33-7 5-biphenyl-4-yl-3,6-dihydro-2H-pyran-4-carboxylic acid ethyl ester 
• 324767-92-2 ethyl 5-hydroxy-3,6-dihydro-2H-pyran-4-carboxylate 
• 127594-84-7 Ethyl 4-<(4-Methoxyphenyl)thio>butanoate 
• 19340-88-6 N-benzyl-4-hydroxybutanamide 
• 1629316-95-5 tert-butyl 2-(4-ethoxy-4-oxobutanoyl)-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 

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