7397-62-8

Basic information

• Product Name: Butyl hydroxyacetate
• Synonyms: N-BUTYL GLYCOLATE;Acetic acid, hydroxy-, butyl ester;Aceticacid,hydroxy-,butylester;hydroxy-aceticacibutylester;hydroxyaceticacidbutylester;BUTYL GLYCOLATE;BUTYL HYDROXYACETATE;butyl glycollate
• CAS NO: 7397-62-8
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.16
• EINECS: 230-991-7
• Product Categories: flow agent in paint
• Mol File: 7397-62-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 187-190 °C(lit.)
• Flash Point: 74 °C
• Appearance: /
• Density: 1.019 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.227mmHg at 25°C
• Refractive Index: n20/D 1.427
• Storage Temp.: 2-8°C
• PKA: 12.99±0.10(Predicted)
• Water Solubility: 46g/L at 20℃
• BRN: 1749477
• CAS DataBase Reference: Butyl hydroxyacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Butyl hydroxyacetate(7397-62-8)
• EPA Substance Registry System: Butyl hydroxyacetate(7397-62-8)

Safety Data

• Hazard Codes: Xn
• Statements: 63-41
• Safety Statements: 23-24/25-36/37/39-26
• RIDADR: NA 1993 / PGIII
• WGK Germany: 1
• Hazardous Substances Data: 7397-62-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Transparent Liquid

Uses

Butyl glycolate may be used in the preparation of N-(α-hydroxyacetyl)-(S)-isoleucine.

General Description

Butyl glycolate is a glycolic acid derivative.

Purification Methods

Dissolve in CHCl3 (EtOH-free), wash with 5% KHCO3 until effervescence ceases (if free acid is present), dry over CaCl2, filter, evaporate and distil through a short column. [B.hme & Opfer Z Anal Chem 139 255 1953, Filachione et al. J Am Chem Soc 73 5265 1951, Beilstein 3 IV 589.]

InChI:InChI=1/C6H12O3/c1-2-3-4-9-6(8)5-7/h7H,2-5H2,1H3

Synthetic route

formaldehyd (50-00-0) + carbon monoxide (201230-82-2) + butan-1-ol (71-36-3) → butyl glycolate (7397-62-8)

Conditions	Yield
Stage #1: formaldehyd; carbon monoxide With 1,3,5-Trioxan; formic acid; sulfuric acid In 1,4-dioxane; dichloromethane at 120℃; under 67506.8 Torr; Stage #2: butan-1-ol In 1,4-dioxane; dichloromethane at 160℃; under 18001.8 Torr; for 40h;	98.3%

glycolic Acid (79-14-1) + butan-1-ol (71-36-3) → butyl glycolate (7397-62-8)

Conditions	Yield
With ion exchange at 120℃; pH=2; pH-value; Temperature; Reagent/catalyst;	92%
With toluene-4-sulfonic acid In cyclohexane for 5h; Reflux;	85.1%
With sulfuric acid; benzene bei langsamer Destillation;

glycolide (502-97-6) + butan-1-ol (71-36-3) → butyl glycolate (7397-62-8)

Conditions	Yield
stannous octoate In hexanoic acid at 135℃;

glycolic Acid (79-14-1) + butan-1-ol (71-36-3) → glycolide (502-97-6) + butyl glycolate (7397-62-8)

Conditions	Yield
With toluene-4-sulfonic acid In cyclohexane for 5h; Reflux;	A n/a B 85.1%

formaldehyd (50-00-0) + butan-1-ol (71-36-3) → butyl glycolate (7397-62-8)

Conditions	Yield
With sulfuric acid; water at 210 - 260℃; under 588406 - 661957 Torr; CO-Druck;

1-bromo-butane (109-65-9) + glycolic Acid (79-14-1) → butyl glycolate (7397-62-8)

Conditions	Yield
With triethylamine for 1h; Heating; Inert atmosphere; Ionic liquid;	87%

Glyoxal (131543-46-9) + butan-1-ol (71-36-3) → butyl glycolate (7397-62-8)

Conditions	Yield
With zeolite MFI-ATSn for 6h; Reagent/catalyst; Time; Sealed tube; Green chemistry;	53%

butan-1-ol (71-36-3) + ammonium glycolate → glycolamide (598-42-5) + butyl glycolate (7397-62-8)

Conditions	Yield
unter Entfernen des entstehenden Wassers und Ammoniaks;

butan-1-ol (71-36-3) + potassium chloroacetate → butyl glycolate (7397-62-8)

butyl glycolate (7397-62-8) + 1,5-difluoro-2,4-dinitrobenzene (327-92-4) → butyl 2,4-dinitro-5-fluorophenoxyacetate (122641-49-0)

Conditions	Yield
With triethylamine In 1,2-dichloro-ethane at 0 - 5℃; for 2h; Large scale;	89.9%

butyl glycolate (7397-62-8) → butyl chloroacetate (590-02-3)

Conditions	Yield
With N,N-dimethyl-formamide; 2-Fluorobenzoyl chloride In 1,4-dioxane at 80℃; for 16h; Sealed tube;	75%

butyl glycolate (7397-62-8) + methyl isocyanate (624-83-9) → 3-(hydroxymethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one (1182358-83-3)

Conditions	Yield
Stage #1: butyl glycolate With hydrazine hydrate at 50℃; for 1h; Stage #2: methyl isocyanate In water at -10 - 20℃; Stage #3: With sodium hydroxide In water at 95℃;	74%

4-[3-(4-chlorophenyl)-4-piperidin-4-yl-1H-pyrazol-5-yl]pyrimidine (271576-76-2) + butyl glycolate (7397-62-8) → 2-{4-[3-(4-chlorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]piperidin-1-yl}-2-oxoethanol (271576-80-8)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene at 110℃; for 3 - 3.41667h;	78%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In xylene; butan-1-ol at 25 - 145℃; Heating / reflux;

butyl glycolate (7397-62-8) + 1,2-dichloro-benzene (95-50-1) → n-butyl o-chlorophenoxyacetate

Conditions	Yield
Stage #1: butyl glycolate With magnesium ethylate at 60℃; Stage #2: 1,2-dichloro-benzene at 90℃;	98.9%

butyl glycolate (7397-62-8) + ortho-cresol (95-48-7) → n-butyl o-tolyloxyacetate

Conditions	Yield
With Mo2P5-MCM-48 at 120℃; for 3h;	99.2%

poly(methacrylic acid) (79-41-4) + butyl glycolate (7397-62-8) → methacrylic butyl glycolate ester

Conditions	Yield
With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃;	20%

butyl glycolate (7397-62-8) + phenol (108-95-2) → butyl 2-phenoxyacetate (32001-59-5)

Conditions	Yield
With catalyst Mo2P5-MCM-48 (molar ratio of Mo2P5 and MCM-48: 25:100) at 100 - 120℃; for 2h; Reagent/catalyst; Time; Temperature;	65.78%

4-[3-(4-chlorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]cyclohexanone (635725-14-3, 857729-86-3) + butyl glycolate (7397-62-8) → 2-{4-[3-(4-chloro-2-fluorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]piperidin-1-yl}-2-oxoethanol

Conditions	Yield
Stage #1: 4-[3-(4-chlorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]cyclohexanone; butyl glycolate With sodium ethanolate In ethanol at 20 - 81℃; for 4h; Stage #2: With hydrogenchloride In ethanol; water at 40℃; Product distribution / selectivity;	70%
Stage #1: 4-[3-(4-chlorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]cyclohexanone; butyl glycolate With sodium ethanolate In ethanol at 20 - 81℃; for 4h; Stage #2: With hydrogenchloride; ethanol; water at 40℃; for 0.166667h;	70%
Stage #1: 4-[3-(4-chlorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]cyclohexanone; butyl glycolate With 1,8-diazabicyclo[5.4.0]undec-7-ene In ethylene glycol at 80℃; for 4.9h; Nitrogen atmosphere; Stage #2: With water In ethylene glycol at 80℃; for 1.25h;

3,4-dihydro-2H-pyran (110-87-2) + butyl glycolate (7397-62-8) → 2-(tetrahydropyran-2-yloxy)-acetic acid butyl ester

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate
With toluene-4-sulfonic acid In dichloromethane at 20 - 35℃; for 16.5h;

butyl glycolate (7397-62-8) + isobutene (115-11-7) → n-butyl 2-tert-butoxyacetate (116193-68-1)

Conditions	Yield
With sulfuric acid In dichloromethane at 25℃; for 72h;	68%
With sulfuric acid In dichloromethane

butyl glycolate (7397-62-8) → butyl glyoxalate (6295-06-3)

Conditions	Yield
With (NH4)4[CuMo6O18(OH)6]·5H2O; oxygen; sodium sulfite In water; acetonitrile at 60℃; under 760.051 Torr; for 12h;	97%

butyl glycolate (7397-62-8) + ethyl vinyl ether (109-92-2) → Vinyloxy-acetic acid butyl ester (213548-19-7)

Conditions	Yield
With mercury(II) diacetate at 0℃; for 21h;	21%
With mercury(II) trifluoroacetate for 1h; Ambient temperature;	15%

butyl glycolate (7397-62-8) + 3-Phenylpropionic acid (501-52-0) → 3-phenyl-propionic acid butoxycarbonylmethyl ester

Conditions	Yield
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h;	91%

3-chloro-2-(2,4-difluoro-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole (121592-85-6) + butyl glycolate (7397-62-8) → 3-chloro-2-(2-fluoro-4-butyloxycarbonylmethoxy-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole (121592-84-5)

Conditions	Yield
With potassium fluoride In 1,4-dioxane
With potassium fluoride In 1,4-dioxane

butyl glycolate (7397-62-8) + trityl chloride (76-83-5) → butyl 2-(trityloxy)acetate (1449782-41-5)

Conditions	Yield
With pyridine at 65℃; for 18h;	96%

2-chloro-3-nitrothiophene (5330-98-3) + butyl glycolate (7397-62-8) → 2-(3-Nitro-2-thienyloxy)essigsaeurebutylester

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 40℃; for 48h;	84%

3-(2,4-difluoro-5-nitrophenyl)-5-methyl-6-trifluoromethylpyrimidine-4-one (153577-85-6) + butyl glycolate (7397-62-8) → 3-(4-butoxycarbonylmethoxy-2-fluoro-5-nitrophenyl)-5-methyl-6-trifluoromethylpyrimidin-4-one

Conditions	Yield
With potassium fluoride In 1,4-dioxane; ethyl acetate

butyl glycolate (7397-62-8) + methanesulfonyl chloride (124-63-0) → n-butyl methylsulfonyloxyacetate

Conditions	Yield
With triethylamine In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane

1-(2-chlorobenzyl)-4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-azepine + butyl glycolate (7397-62-8) → Butyl 6-(2-chlorobenzyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine-2-carboxylate

Conditions	Yield
With nitrogen In 1,4-dioxane; chloroform; water; ethyl acetate

furan-2,5-dicarboxylic acid (3238-40-2) + butyl glycolate (7397-62-8) → furandiformyl-butyl glycolate

Conditions	Yield
With toluene-4-sulfonic acid at 160℃;

3-diazo-1-methyl-1,3-dihydro-indol-2-one (3265-14-3) + butyl glycolate (7397-62-8) → butyl 2-((1-methyl-2-oxoindolin-3-yl)oxy)acetate

Conditions	Yield
In dichloromethane at 25℃; for 24h; Irradiation;	56%

1H-imidazole (288-32-4) + butyl glycolate (7397-62-8) + tert-butyldimethylsilyl chloride (18162-48-6) → n-butyl <(tert-butyldimethylsilyl)oxy>acetate (114790-31-7)

Conditions	Yield
In hexane
In hexane

butyl glycolate (7397-62-8) → 4-cyano-5-methyl-tetrahydrofuran-3-one (70097-89-1)

Conditions	Yield
In tetrahydrofuran

Upstream product

• 50-00-0 formaldehyd 
• 71-36-3 butan-1-ol 
• 79-14-1 glycolic Acid 
• 502-97-6 glycolide 
• 109-65-9 1-bromo-butane 
• 131543-46-9 Glyoxal 
• 201230-82-2 carbon monoxide 

Downstream Products

• 93759-10-5 [(2,4,5-trichloro-phenoxy)-acetoxy]-acetic acid butyl ester 
• 109-11-5 morpholine-3-one 
• 54145-95-8 3-methyl-4-oxo-trans-crotonic acid butyl ester 
• 14658-93-6 2-hydroxy-N,N-dimethylacetamide 
• 121592-84-5 3-chloro-2-(2-fluoro-4-butyloxycarbonylmethoxy-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole 
• 122641-49-0 butyl 2,4-dinitro-5-fluorophenoxyacetate 
• 590-02-3 butyl chloroacetate 
• 6295-06-3 butyl glyoxalate 
• 1713-12-8 n-butyl 4-chloro-2-methylphenoxyacetate 
• 32001-59-5 butyl 2-phenoxyacetate 
• 1182358-83-3 3-(hydroxymethyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one 
• 1449782-41-5 butyl 2-(trityloxy)acetate 
• 271576-80-8 2-{4-[3-(4-chlorophenyl)-4-pyrimidin-4-yl-1H-pyrazol-5-yl]piperidin-1-yl}-2-oxoethanol 
• 87826-74-2 2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-n-butylester 

Relevant articles and documents

Preparation method of glycolic acid or glycolate

The invention discloses a preparation method of glycolic acid or glycolate. The method comprises the following steps of: formaldehyde and carbon monoxide are introduced into a reactor containing a reaction solution to carry out polymerization reaction, wherein the reaction solution contains an acid catalyst; after the relative molecular mass of a polymer generated by the polymerization reaction reaches 2,000 and above, the polymerization reaction system is cooled to crystallize and precipitate the generated polymer; solid-liquid separation is carried out on the material in the reactor; and excessive water or alcohol is added into the obtained solid phase to carry out a depolymerization reaction to obtain glycolic acid or glycolate. Compared with the prior art, the method disclosed by the invention is good in process stability, low in energy consumption, good in economic practicability and high in product yield, and has a very good application prospect.

Preparation method of chlorophenoxyacetic ester

The invention provides a preparation method of chlorophenoxyacetic ester, wherein the preparation method comprises the following steps: A) carrying out reaction of glycolic acid and alcohol in tolueneto obtain glycolic ester; B) carrying out reaction of glycolic ester and metal alkoxide to obtain a metal salt of glycolic ester; and C) carrying out reaction of the metal salt of glycolic ester andchlorobenzene to obtain the chlorophenoxyacetic ester. The chlorophenoxyacetic ester is synthesized by condensation of chlorobenzene with the metal salt of glycolic ester, the use of chlorophenol withunpleasant odor is effectively avoided, the production of highly toxic dioxins is eliminated, and the product quality and the operating environment of the production site are greatly improved. Motherliquor containing effective ingredients cannot be produced, so the loss of effective ingredients is effectively avoided and the yield of the product is improved.

Natural preservatives

In the present invention, provided is a compound, which has good antibacterial effects and is denoted by general formula (I), or a pharmaceutical acceptable salt thereof where R1 is saturated or unsaturated straight chains or branch chains of an alkyl group in general formula (I); R2 is hydrogen, methyl or is selected from a general formula (2); and R3 is hydrogen, saturated or unsaturated straight chains or branch chains of an alkyl group, and X is hydrogen or is selected from a hydroxyl group in general formula (2).COPYRIGHT KIPO 2015