3068-00-6

Basic information

• Product Name: 1,2,4-Butanetriol
• Synonyms: Butanetriol,97%;1 2 4-BUTANETRIOL 96%;trihydroxybutane;1,2,4-BUTANETRIOL 99.5%;1,2,4-BUTANETRIOL 98+%;1,2,4-Butanetriol,95%;Dutane-1,2,4-triol;4-Butanetriol
• CAS NO: 3068-00-6
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.12
• EINECS: 221-323-5
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 3068-00-6.mol
• Article Data: 45

Chemical Properties

• Melting Point: -20°C
• Boiling Point: 190-191 °C18 mm Hg(lit.)
• Flash Point: 188°C
• Appearance: clear yellow to slightly brownish liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.63E-05mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO, Water
• PKA: 14.02±0.20(Predicted)
• Sensitive: Hygroscopic
• BRN: 1733456
• CAS DataBase Reference: 1,2,4-Butanetriol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Butanetriol(3068-00-6)
• EPA Substance Registry System: 1,2,4-Butanetriol(3068-00-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• WGK Germany: 1
• RTECS: EK7176000
• TSCA: Yes
• Hazardous Substances Data: 3068-00-6(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to slightly brownish liquid

Uses

1,2,4-Butanetriol was used as starting reagent during the synthesis of a series of quaternary ammonium lipids. It was also used in the synthesis of (-)-γ-amino-8-hydroxy butyric acid (GABOB), antiepileptic and hypotensive drug.

Definition

ChEBI: A triol that is butane carrying three hydroxy substituents at position 1, 2 and 4.

InChI:InChI=1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2/t4-/m1/s1

Synthetic route

malic acid (617-48-1) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With hydrogen; 5% activated charcoal-supported ruthenium catalyst In ethanol at 120℃; under 120012 Torr; for 70 - 90h; Product distribution / selectivity;	90%
In water	77%
With hydrogen; 5% activated charcoal-supported ruthenium catalyst In water at 100 - 120℃; under 7500.75 - 90009 Torr; for 6 - 24h; Product distribution / selectivity;	63%

maleamide (928-01-8) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With ruthenium on silica; hydrogen In tetrahydrofuran at 200℃; under 75007.5 Torr; for 12h; Temperature; Pressure; Time;	87%

malic acid dimethyl ester (38115-87-6) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With hydrogen; CuO/ZnO/Al2O3 In tetrahydrofuran at 180℃; under 7500.75 - 75007.5 Torr; for 4h; Product distribution / selectivity;	80%
With potassium tert-butylate In 1,4-dioxane at 70℃; for 48h; Temperature; Time;	62%
With potassium borohydride In ethanol
With hydrogenchloride; sodium borohydrid In tetrahydrofuran; methanol; isopropyl alcohol; acetone
With hydrogen; [(MeC(CH2PPh2)3)Ru(acetonitrile)3](CF3SO3)2 In methanol at 100℃; under 30003 Torr; for 14h; Product distribution / selectivity; Inert atmosphere; Autoclave;	>= 99.9 %Chromat.

malic acid (617-48-1) → propylene glycol (57-55-6) + Butane-1,4-diol (110-63-4) + D,L-1,2,4-butanetriol (3068-00-6) + ethylene glycol (107-21-1)

Conditions	Yield
With hydrogen; Ru-carbon In water at 135℃; under 258574 Torr; for 10h; Further byproducts given;	A 11% B 8% C 74% D 3%

homoalylic alcohol (627-27-0) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
Stage #1: homoalylic alcohol With formic acid; water; dihydrogen peroxide at 55 - 60℃; for 7h; Stage #2: With methanol; Marlon-AS3 at 55 - 85℃; for 3h;	72%
With sulfuric acid; water; dihydrogen peroxide
Stage #1: homoalylic alcohol With sodium periodate; acetic acid; lithium bromide at 95℃; for 18h; Prevost-Woodward reaction; Stage #2: With potassium carbonate In methanol at 25℃; for 24h;
With potassium permanganate

rac-3,4-dihydroxybutyl bromide (33835-83-5) → D,L-1,2,4-butanetriol (3068-00-6) + rac-3,4-dihydroxybutylarsonic acid

Conditions	Yield
With 3-Hydroxytetrahydrofuran; trisodium arsenite; hydrogen bromide for 96h; Ambient temperature;	A 5% B 17%

diethylmalate (7554-12-3) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With copper chromite; ethanol at 100 - 150℃; under 257428 Torr; Hydrogenation;
With ethanol; nickel at 100 - 150℃; under 257428 Torr; Hydrogenation;

1,4-dihydroxy-2-butanone (140-86-3) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With water; nickel at 60 - 100℃; under 147102 Torr; Hydrogenation;
With copper oxide-chromium oxide; water; silica gel at 80 - 100℃; under 147102 Torr; Hydrogenation;

formaldehyd (50-00-0) → D,L-1,2,4-butanetriol (3068-00-6) + 1,2,3,4-butanetetrol (2319-57-5, 2418-52-2, 6968-16-7, 7493-90-5, 7541-59-5) + ethylene glycol (107-21-1) + 2-C-hydroxymethyltetritol (89615-91-8) + glycerol (56-81-5) + sorbitol (50-70-4, 69-65-8, 87-78-5, 133-43-7, 488-44-8, 488-45-9, 608-66-2, 643-01-6, 643-03-8, 5552-13-6, 6706-59-8, 24557-79-7, 25878-23-3, 26566-34-7, 45007-61-2, 60660-56-2, 60660-57-3, 60660-58-4, 132747-27-4)

Conditions	Yield
With calcium oxide Product distribution; Heating; reduction of formed monosacharides;;

3-Benzoyloxytetrahydrofuran (131076-15-8, 79677-01-3) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With titanium tetrachloride 1) CH2Cl2, 72h, reflux 2) saponification; Multistep reaction;

4-Methoxy-benzoic acid tetrahydro-furan-3-yl ester (129956-99-6) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With titanium tetrachloride; potassium carbonate 1) CH2Cl2, 72h, reflux 2) MeOH, 10h, r.t.; Yield given. Multistep reaction;

2-6'-acetoxy-6'-formyloxy-4'-oxo-2'-hexenamido-3-hydroxy-2-cyclopenten-1-one (82644-93-7) → D,L-1,2,4-butanetriol (3068-00-6) + 2-glycolamido-3-hydroxy-2-cyclopenten-1-one (80548-64-7)

Conditions	Yield
With sodium tetrahydroborate; ozone 1.) dichloromethane, cooled with dry ice-acetone, 40 min.; 2.) ethanol, water, 30 min, cooling; room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given;
With sodium tetrahydroborate; ozone 1.) dichloromethane, cooled with dry ice-acetone, 40 min.; 2.) ethanol, water, 30 min. cooling; room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

D-2-deoxyribose (452-51-7, 13046-70-3, 29780-54-9, 36792-87-7, 36792-88-8, 113890-35-0, 113890-38-3) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; RhCl(PPh3)3 at 130℃; for 0.5h;	90 % Chromat.

homoalylic alcohol (627-27-0) → 3-Hydroxytetrahydrofuran (453-20-3) + D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With titanium silicate; dihydrogen peroxide at 24.9℃; for 6h; Title compound not separated from byproducts;

Adipic acid (124-04-9) + NaNO3 + platinum anode + nitric acid ester → butane-1,2,3-triol (4435-50-1) + D,L-1,2,4-butanetriol (3068-00-6) + meso-erythritol (909878-64-4) + ethylene glycol (107-21-1)

Conditions	Yield
Das Natriumsalz bei der reduzierenden Verseifung mit Ba(SH)2 in Butandiol-(1.2);

(+-)-1,2,4-triacetoxy-butane → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With hydrogenchloride; methanol
With methanol; sulfuric acid

salt of/the/ 3-isopentyloxy-propionic acid → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With sodium nitrate Electrolysis.an einer Platinanode und reduzierende Verseifung des Reaktionsgemisches mit Ba(SH)2;

salt of/the/ adipic acid → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With sodium nitrate Electrolysis.an einer Platinanode und reduzierende Verseifung des Reaktionsgemisches mit Ba(SH)2;

salt of/the/ levulinic acid → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With sodium nitrate Electrolysis.an einer Platinanode und reduzierende Verseifung des Reaktionsgemisches mit Ba(SH)2;

homoalylic alcohol (627-27-0) + KMnO4 → D,L-1,2,4-butanetriol (3068-00-6)

1,4-dihydroxy-2-butanone (140-86-3) + water (7732-18-5) + Raney nickel → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
at 60 - 100℃; under 147102 Torr; Hydrogenation;

triacetate of butanetriol-(1.2.4) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With barytes

1,2-dibromo-4-methoxy-butane (7124-16-5) + water (7732-18-5) → 3-Hydroxytetrahydrofuran (453-20-3) + D,L-1,2,4-butanetriol (3068-00-6) + 4-methoxy-1,2-butanediol (90325-06-7)

dimethyl (S)-malate (617-55-0) → D,L-1,2,4-butanetriol (3068-00-6) + (3S)-3-hydroxydihydrofuran-2(3H)-one (52079-23-9) + 2-buten-4-olide (497-23-4) + methyl 3,4-dihydroxybutanoate (88246-12-2)

Conditions	Yield
With hydrogen In Dimethyl ether at 56 - 110℃; under 120012 Torr; for 0.5 - 2h; Product distribution / selectivity;	A n/a B n/a C n/a D n/a

cis-2,3-epoxy-1,4-butanediol (4440-87-3) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With hydrogen; Ni(30 wt%)/SiO2 In isopropyl alcohol at 90 - 120℃; under 68404.6 Torr; Product distribution / selectivity;
With hydrogen; nickel In isopropyl alcohol at 120℃; under 68404.6 Torr; for 6h; Product distribution / selectivity;
With hydrogen; 5%-palladium/activated carbon In isopropyl alcohol at 120℃; under 68404.6 Torr; for 5h; Product distribution / selectivity;

(R)-dimethyl malate (70681-41-3) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water
With sodium hydroxide In tetrahydrofuran; water

4-butanolide (96-48-0) → D,L-1,2,4-butanetriol (3068-00-6)

Conditions	Yield
In tetrahydrofuran

D-sorbitol (50-70-4) → propylene glycol (57-55-6) + ethanol (64-17-5) + 1.3-butanediol (18826-95-4, 107-88-0) + D,L-1,2,4-butanetriol (3068-00-6) + XYLITOL (87-99-0) + ethylene glycol (107-21-1) + isopropyl alcohol (67-63-0) + glycerol (56-81-5) + 2.3-butanediol (513-85-9) + 1,2-dihydroxybutane (584-03-2)

Conditions	Yield
With potassium hydroxide; hydrogen; nickel-rhenium-on-carbon In water at 220℃; under 31029.7 - 62059.4 Torr; for 4h; Product distribution / selectivity;

...Expand

Dimethoxymethane (109-87-5) + D,L-1,2,4-butanetriol (3068-00-6) → (1,3-dioxan-4-yl)methanol (4728-06-7)

Conditions	Yield
	100%

D,L-1,2,4-butanetriol (3068-00-6) + benzoyl chloride (98-88-4) → (+/-)-1,2,4-tris(benzoyloxy)butane (129956-98-5)

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 25℃;	100%

D,L-1,2,4-butanetriol (3068-00-6) + 2,2-diphenylacetaldehyde dimethyl acetal (51936-06-2) → 2-(2-benzhydryl-1,3-dioxolan-4-yl)ethan-1-ol

Conditions	Yield
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; for 17h;	100%

D,L-1,2,4-butanetriol (3068-00-6) + orthobenzoic acid trimethyl ester (707-07-3) → 3-Benzoyloxytetrahydrofuran (131076-15-8, 79677-01-3)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 2h;	99%

D,L-1,2,4-butanetriol (3068-00-6) → 3-Hydroxytetrahydrofuran (453-20-3)

Conditions	Yield
sulfuric acid at 140℃; under 49.505 Torr; Product distribution / selectivity; Reactive distillation; Intramolecular dehydration;	98%
samarium(III) trifluoromethanesulfonate at 140℃; under 49.505 Torr; Product distribution / selectivity; Reactive distillation; Intramolecular dehydration;	97%
strong acid ion exchange resin (Amberlyst 15, H+ form) In 1,4-dioxane at 100℃; under 760.051 Torr; for 20h; Product distribution / selectivity;	96%

D,L-1,2,4-butanetriol (3068-00-6) + acetone (67-64-1) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With toluene-4-sulfonic acid at 20℃; for 4h;	98%
With toluene-4-sulfonic acid at 20℃; for 20h;	97%
With toluene-4-sulfonic acid	86%

D,L-1,2,4-butanetriol (3068-00-6) + cyclohexanone (108-94-1) → 2-(1,4-dioxa-spiro[4.5]dec-2-yl)-ethanol (616876-76-7)

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃;	97%

D,L-1,2,4-butanetriol (3068-00-6) + 2,2-dimethoxy-propane (77-76-9) → (2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanol (61821-85-0)

Conditions	Yield
In dichloromethane	96.7%

D,L-1,2,4-butanetriol (3068-00-6) → barium D-butane-1,2,4-triol-1-phosphate barium

Conditions	Yield
With water-d2; phospho(enol)pyruvic acid mono potassium salt; adenosine 5'-triphosphate disodium salt; barium(II) chloride; magnesium chloride; glycerol kinase from S. cerevisiae or from E. coli and pyruvate kinase In various solvent(s) for 1h;	95%

D,L-1,2,4-butanetriol (3068-00-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 1,4-di(tert-butyldimethylsilanyloxy)butan-2-ol (631899-30-4)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃;	95%
With 1H-imidazole In dichloromethane Inert atmosphere; chemoselective reaction;
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Cooling;

D,L-1,2,4-butanetriol (3068-00-6) + didocosahexanoyl ketone → 2,2-didocosahexaenoyl-4-(2-hydroxyethyl)-[1,3]-dioxolane

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene Reflux; Inert atmosphere; Dean-Stark;	95%

D,L-1,2,4-butanetriol (3068-00-6) + (6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-one (1169768-30-2) → 2,2-dilinoleyl-4-(2-hydroxyethyl)-[1,3]-dioxolane (1190203-55-4)

Conditions	Yield
With toluene-4-sulfonic acid for 3h; Reflux; Molecular sieve;	90%
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark;	47%
With pyridinium p-toluenesulfonate In toluene Reflux; Inert atmosphere;
With pyridinium p-toluenesulfonate In toluene
With pyridinium p-toluenesulfonate In toluene Inert atmosphere; Reflux; Dean-Stark tube;

D,L-1,2,4-butanetriol (3068-00-6) + heptatriaconta-6,9,28,31-tetraen-19-one → C41H74O3

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 3h; Reflux; Molecular sieve;	90%
With toluene-4-sulfonic acid In toluene for 3h; Reflux; Molecular sieve;	90%

D,L-1,2,4-butanetriol (3068-00-6) + (benzoyloxy)acetaldehyde diethyl acetal (101268-52-4) → cis-[4-(hydroxymethyl)-1,3-dioxan-2-yl]methyl benzoate

Conditions	Yield
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; for 0.1h; stereoselective reaction;	90%

D,L-1,2,4-butanetriol (3068-00-6) + 1-amino-3-methylbenzene (108-44-1) → 1-m-tolyl-pyrrolidin-3-ol (5422-64-0)

Conditions

Yield

Stage #1: D,L-1,2,4-butanetriol With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 0.666667h; Molecular sieve; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: 1-amino-3-methylbenzene In toluene at 20℃; for 48.33h; Inert atmosphere; Schlenk technique; Sealed tube; Reflux; Green chemistry;

90%

D,L-1,2,4-butanetriol (3068-00-6) + hexaethylphosphoric triamide (2283-11-6) → 2,7,8-trioxa-1-phosphabicyclo<3.2.1>octane (13232-18-3)

Conditions	Yield
at 100℃;	89%

3-chloro-1,1-diethoxy-propane (35573-93-4) + D,L-1,2,4-butanetriol (3068-00-6) → cis-[2-(2-chloroethyl)-1,3-dioxan-4-yl]methanol

Conditions	Yield
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction;	89%

D,L-1,2,4-butanetriol (3068-00-6) + ethenyltrimethylsilane (754-05-2) → 1,2,4-Tris-trimethylsiloxy-butan (33581-75-8)

Conditions	Yield
Wilkinson's catalyst In toluene at 130℃; for 6h;	88%

D,L-1,2,4-butanetriol (3068-00-6) + benzaldehyde (100-52-7) → (+/-)-cis-4-(hydroxymethyl)-2-phenyl-1,3-dioxane (3969-69-5, 72258-22-1, 93351-55-4, 95840-93-0, 103773-79-1)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 4.5h; Heating;	87%
With toluene-4-sulfonic acid In toluene for 1h; Reflux;	53%
With molecular sieve; toluene-4-sulfonic acid In toluene Heating;

(1,3-bis(diphenylphosphino)propane)Pt(CO3) (156053-80-4) + D,L-1,2,4-butanetriol (3068-00-6) → [(1,3-bis(diphenylphosphino)propane)]platinum(II)(1,2,4-butanetriolate) (156053-65-5)

Conditions	Yield
In dichloromethane byproducts: CO2, H2O; under Ar; Pt-complex and 1.05 equiv of the triol dissolved in CH2Cl2, soln. stirred 2 h, soln. purged with Ar 4 times over a period of 3 h; evapn. (vac.), dried (vac., 1 h), dissolved in min. amt. CH2Cl2, layered with ether (crystn.), cryst. isolated, dried (vac.), elem. anal.;	87%

D,L-1,2,4-butanetriol (3068-00-6) + benzyl chloride (100-44-7) → (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane (94426-71-8)

Conditions	Yield
With sodium hydride; sodium iodide In N,N-dimethyl-formamide for 12h; Ambient temperature;	86%

D,L-1,2,4-butanetriol (3068-00-6) + C41H82O (1260142-20-8) → C45H90O3 (1260142-21-9)

Conditions	Yield
With pyridinium p-toluenesulfonate In toluene Inert atmosphere; Reflux;	86%

D,L-1,2,4-butanetriol (3068-00-6) + m-Anisidine (536-90-3) → 1-(3-methoxy-phenyl)-pyrrolidin-3-ol (536742-58-2)

Conditions

Yield

Stage #1: D,L-1,2,4-butanetriol With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 0.666667h; Molecular sieve; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: m-Anisidine In toluene at 20℃; for 48.33h; Inert atmosphere; Schlenk technique; Sealed tube; Reflux; Green chemistry;

86%

D,L-1,2,4-butanetriol (3068-00-6) → 1,4-dihydroxy-2-butanone (140-86-3)

Conditions	Yield
With C30H42N4O6Pd2(2+)*2CF3O3S(1-); p-benzoquinone In water; acetonitrile at 55℃; for 24h; Darkness; chemoselective reaction;	85%
With Candida boidinii KK912 In methanol; water at 30℃; for 48h; phosphate buffer (pH=7); other butanols;	78.1%
With phosphate buffer; Candida boidinii KK912 In methanol; water at 30℃; for 48h;	78.1%
With [(neocuproine)Pd(OAc)]2(OTf)2; oxygen In water; acetonitrile at 25℃; for 20h; Reagent/catalyst; Temperature; chemoselective reaction;	71%
With 2-Picolinic acid; manganese(II) perchlorate hexahydrate; butanedial; dihydrogen peroxide; sodium acetate In acetonitrile at 0 - 20℃; for 1h; Solvent;

D,L-1,2,4-butanetriol (3068-00-6) + 2,2-dimethoxy-propane (77-76-9) → 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (5754-34-7)

Conditions	Yield
With camphor-10-sulfonic acid	85%
With camphor-10-sulfonic acid In acetonitrile at 20℃;	80%
Stage #1: D,L-1,2,4-butanetriol; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20℃; for 4h; Reflux; Stage #2: In methanol at 0℃; for 12h;	74%

D,L-1,2,4-butanetriol (3068-00-6) + Bromoacetaldehyde diethyl acetal (2032-35-1) → cis-[2-(bromomethyl)-1,3-dioxan-4-yl]methanol

Conditions	Yield
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction;	85%

D,L-1,2,4-butanetriol (3068-00-6) + benzaldehyde dimethyl acetal (1125-88-8) → (+/-)-cis-4-(hydroxymethyl)-2-phenyl-1,3-dioxane (3969-69-5, 72258-22-1, 93351-55-4, 95840-93-0, 103773-79-1)

Conditions	Yield
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction;	84%

Upstream product

• 617-48-1 malic acid 
• 7554-12-3 diethylmalate 
• 140-86-3 1,4-dihydroxy-2-butanone 
• 38115-87-6 malic acid dimethyl ester 
• 50-00-0 formaldehyd 
• 82644-93-7 2-6'-acetoxy-6'-formyloxy-4'-oxo-2'-hexenamido-3-hydroxy-2-cyclopenten-1-one 
• 33835-83-5 rac-3,4-dihydroxybutyl bromide 
• 627-27-0 homoalylic alcohol 
• 124-04-9 Adipic acid 
• 617-55-0 dimethyl (S)-malate 
• 909878-64-4 meso-erythritol 
• 5469-16-9 4-Hydroxy-dihydro-furan-2-on 
• 928-01-8 maleamide 
• 453-20-3 3-Hydroxytetrahydrofuran 

Downstream Products

• 453-20-3 3-Hydroxytetrahydrofuran 
• 854841-54-6 2,5-bis-(2-hydroxy-ethyl)-[1,4]dioxane 
• 2419-74-1 1,4-dichlorobutan-2-ol 
• 19398-47-1 1,4-dibromo-2-butanol 
• 14835-47-3 1,2,4-trihydroxybutane triacetate 
• 6659-60-5 1,2,4-butanetriol trinitrate 
• 5422-64-0 1-m-tolyl-pyrrolidin-3-ol 
• 5754-34-7 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane 
• 56476-33-6 (2,2-dimethyl-[1,3]dioxan-4-yl)-methanol 
• 32233-43-5 2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol 
• 85287-64-5 (S)-butane-1,2,4-triol 2,4-acetonide 
• 42890-76-6 (S)-1,2,4-butanetriol 
• 70005-88-8 (R)-1,2,4-butanetriol 
• 94426-71-8 (+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane 

Relevant articles and documents

A new antiangiogenic C24 oxylipin from the soft coral Sinularia numerosa

A new oxylipin, 15-hydroxy-tetracosa-6,9,12,16,18-pentaenoic acid (15-HTPE; 1) was isolated as an inhibitor of tube-formation from the soft coral Sinularia numerosa. Its structure was elucidated by means of spectral analysis and chemical degradation. 15-H

Ru/SiO2 Catalyst for Highly Selective Hydrogenation of Dimethyl Malate to 1,2,4-Butanetriol at Low Temperatures in Aqueous Solvent

Catalytic selective hydrogenation of esterified malic acid to produce 1,2,4-butanetriol (1,2,4-BT) using H2 as the reducing reagent suffers from the low 1,2,4-BT selectivity. Here, Ru/SiO2 catalyst was employed for selective hydrogenation of dimethyl malate (DM) to produce 1,2,4-BT, which gave abnormal high DM conversion (100%) and 1,2,4-BT selectivity (92.4%) in aqueous solvent at 363?K, especially, the 1,2,4-BT yield even is higher than the optimal catalyst reported (Ru-Re, 79.8%). The reaction pathways for the DM hydrogenation on Ru/SiO2 were also proposed, suggesting that extremely high 1,2,4-BT selectivity require for the much high hydrogenation rates at low temperatures, where side-reaction transesterification rates are relatively low. The extremely high hydrogenation activity and 1,2,4-BT selectivity on Ru/SiO2 in aqueous solvent at low temperatures arise from that H2O may coordinate to Ru2+ and prevent the reduction of Ru2+ to Ru under high H2 pressure. Ru/SiO2 surface presents abundant Ru2+ in aqueous solvent, can activate H2 through heterolytic cleavage mode to form hydride, which can significantly increase hydrogenation rates of C = O groups at low temperatures. In addition, the activity and 1,2,4-BT selectivity on Ru/SiO2 catalyst only reduced by 2.3% and 2.6%, respectively over a period of 550?h. Graphical Abstract: [Figure not available: see fulltext.]

Method for preparing 1,2,4-butantriol through reduction of hydrosilane

The invention discloses a method for preparing 1,2,4-butantriol through reduction of hydrosilane. According to the method, dimethyl malate is selectively reduced into 1,2,4-butantriol under the condition that dioxane is used as a solvent by taking polymethylhydrosiloxane as a reducing agent and potassium tert-butoxide as a catalyst, wherein the reducing agent is low in price, the reaction condition is mild, the selectivity of 1,2,4-butantriol is 100%, and the yield reaches 70%.