4457-71-0

Usage

Chemical Properties

Colorlessliquid

Uses

3-Methyl-1,5-pentanediol is a reagent used in the preparation of lactones from diols using molecular oxygen oxidant and hydrotalcite-supported gold nanoparticles catalysts under mild conditions.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C6H14O2/c1-6(2-4-7)3-5-8/h6-8H,2-5H2,1H3

Synthetic route

3-methylglutaric anhydride (4166-53-4) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;	100%
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating;	68%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Reduction;	44%
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 6.5h; Heating;	33%
With lithium aluminium tetrahydride In tetrahydrofuran

4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol (18653-57-1) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With water; hydrogen; sodium hydroxide at 120℃; under 6000.6 Torr; for 6h; Reagent/catalyst;	95%
With hydrogen; sodium hydroxide In water at 120℃; under 6000.6 Torr; for 7h;

3-methyl glutaric acid (626-51-7) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With borane-THF for 18h; Heating;	75%
With lithium aluminium tetrahydride; diethyl ether
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h;
Multi-step reaction with 2 steps 1: H2SO4 2: sodium; ethanol View Scheme

dimethyl 3-methylglutarate (19013-37-7) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With lithium aluminium tetrahydride	75%
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating;

4-(β-hydroxyethyl)-4-methyl-1,3-dioxane (2018-45-3) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With hydrogen; copper at 240℃; under 225018 Torr; for 5h;	65%

3,4-dihydro-2-methoxy-4-methyl-2H-pyran (38113-08-5, 38320-49-9, 53608-95-0) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With copper oxide-chromium oxide; water; hydrogen at 180℃; under 144160 Torr;
With hydrogen; nickel; acetic acid at 150℃; under 66195.7 Torr;

6-methoxy-4-methyl-3,6-dihydro-2H-pyran (59677-19-9) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With hydrogenchloride und Hydrieren des Reaktionsgemisches an Raney-Nickel in neutraler Loesung bei 125grad;

diethyl 3-methylglutarate (6829-42-1) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With copper oxide-chromium oxide Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With ethanol; sodium

3-methylpentanedial (6280-15-5) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With ethanol; nickel at 100℃; under 36775.4 Torr; Hydrogenation;

3-methylenepentane-1,5-diol (40760-35-8) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With 1,4-dioxane; nickel at 100℃; under 257428 Torr; Hydrogenation;

1,5-diacetoxy-3-methylpentane (40065-27-8) + sodium methylate (124-41-4) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With methanol

3-methyl-5-oxo-pentanoic acid methyl ester (5898-67-9) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With lithium aluminium tetrahydride

3-methyl-2.4-diethoxycarbonyl-glutaric acid diethyl ester → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With copper chromite; hydrogen at 250℃; unter Druck;

tetraethyl 2-methylpropane-1,1,3,3-tetracarboxylate (4525-30-8) + copper chromite → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
at 250℃; under 147102 - 220652 Torr;

dimethyl glutaconate (5164-76-1) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: CuI / tetrahydrofuran / 20 °C 1.2: TMSCl / tetrahydrofuran / -78 - 20 °C 2.1: lithium aluminum hydride / tetrahydrofuran / 24 h / Heating View Scheme

2-ethoxy-4-methyl-3,4-dihydro-2H-pyran (10138-44-0) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: Raney nickel; ethanol / 100 °C / 36775.4 Torr / Hydrogenation View Scheme

2-methyl-1-buten-4-ol (763-32-6) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 200 °C 2: Raney nickel; dioxane / 100 °C / 257428 Torr / Hydrogenation View Scheme
Multi-step reaction with 3 steps 1.1: A-36 ion exchange resin / 100 °C / 1200.12 Torr / Autoclave; Large scale 1.2: hollow molecular sieve nanotubes supported silicotungstic acid catalyst / 105 - 155 °C / 825.08 Torr / Large scale 2.1: dicarbonyl(acetylacotonato)rhodium(I); C72H100O6P2; hydrogen / 24 h / 125 °C / 75007.5 Torr / Flow reactor 3.1: hydrogen / 150 - 240 °C / 1200.12 Torr / Flow reactor View Scheme

Methyl 3,3-dimethylacrylate (924-50-5) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Co2(CO)8 / 140 °C / 132391 Torr 2: LiAlH4 View Scheme

Di-n-octyl phthalate (117-84-0) + 4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol (18653-57-1) → 4-methyl-tetrahydro-pyran-2-one (1121-84-2) + 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With manganese dioxide; copper chromite

4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol (18653-57-1) → 4-methyl-tetrahydro-pyran-2-one (1121-84-2) + 3-methylpentane-1,5-diol (4457-71-0) + MPAE (956007-32-2)

Conditions	Yield
With sodium hydroxide; hydrogen; nickel In water at 120℃; under 6600.66 Torr; for 5h; pH=8.4 - 10.9; Product distribution / selectivity;
With hydrogen In water at 120℃; for 2h; Product distribution / selectivity;
With hydrogen; cobalt In water at 120℃; for 5h; Product distribution / selectivity;

molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With hydrogen In 1,4-dioxane

4-methyl-5,6-dihydro-2H-pyran-2-one (2381-87-5) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With dicarbonylacetylacetonato rhodium (I); hydrogen; molybdenum hexacarbonyl In 1,4-dioxane at 200℃; under 90009 - 112511 Torr; for 2.33333h; Schlenk technique; Autoclave;
With 5 wt% ruthenium/carbon; hydrogen In water at 100℃; under 105011 Torr; for 6.3h;
With ruthenium-carbon composite; hydrogen In water at 100℃; under 105011 Torr; for 16h; Catalytic behavior; Temperature; Pressure;

α-methyl-δ-valerolactone (73746-79-9, 80698-15-3, 107242-87-5, 10603-03-9, 823-22-3) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With 5 wt% ruthenium/carbon; hydrogen In water at 100℃; under 105011 Torr; for 6.3h;

mevalonolactone (674-26-0) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With ruthenium-carbon composite; hydrogen In water at 100℃; under 105011 Torr; for 3.5h; Catalytic behavior; Time;

D,L-mevalonic acid (150-97-0, 690-72-2, 17817-88-8, 32451-23-3) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 15 h / Reflux 2: hydrogen; ruthenium-carbon composite / water / 3.5 h / 100 °C / 105011 Torr View Scheme

3-methyl-5-oxopentyl acetate (101153-84-8) → 3-methylpentane-1,5-diol (4457-71-0)

Conditions	Yield
With hydrogen at 150 - 240℃; under 1200.12 Torr; Flow reactor;

3-methylpentane-1,5-diol (4457-71-0) → 4-methyltetrahydropyran (4717-96-8)

Conditions	Yield
With toluene-4-sulfonic acid at 135℃; for 41h;	99.6%
With Amberlyst 15	91%
With toluene-4-sulfonic acid at 135 - 155℃; Dean-Stark; Large scale;	3662 g
With toluene-4-sulfonic acid at 135 - 155℃; for 41h; Large scale;
With toluene-4-sulfonic acid at 135 - 155℃;

3-methylpentane-1,5-diol (4457-71-0) → (S)-4-methyltetrahydro-2H-pyran-2-one (61898-56-4)

Conditions	Yield
With horse liver alcohol dehydrogenase; oxygen; catalase; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride In aq. phosphate buffer at 20℃; for 13h; pH=8; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	97%
With 2,6-dimethylpyridine; sodium perchlorate In acetonitrile for 10h; Electrolysis;	96.4%
With sodium perchlorate; (-)-sparteine In acetonitrile macroelectrolysis with 2,2,6,6-tetramethylpiperidine-1-yloxyl)-modified graphite felt electrodes;	93.8%

3-methylpentane-1,5-diol (4457-71-0) + p-toluenesulfonyl chloride (98-59-9) → 3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate) (148054-23-3)

Conditions	Yield
With dmap; triethylamine In acetonitrile at 20℃; for 3h;	97%
With triethylamine In dichloromethane at 20℃; for 18h;	82.5%
With pyridine at 20℃; for 2h;
With pyridine at 20℃; for 1h;

3-methylpentane-1,5-diol (4457-71-0) → 4-methyl-tetrahydro-pyran-2-one (1121-84-2)

Conditions	Yield
With oxygen In toluene at 110℃; for 1h;	96%
With hydrotalcite-supported copper nanoparticles In 1,3,5-trimethyl-benzene at 150℃; for 8h; Inert atmosphere;	96%
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry;	96%

3-methylpentane-1,5-diol (4457-71-0) + benzylamine (100-46-9) → 1-benzyl-4-methylpiperidine (14446-71-0)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 16h; Microwave irradiation; Inert atmosphere; Sealed tube;	96%
With 1,4-dioxane; copper oxide-chromium oxide; hydrogen at 250℃; under 147102 - 294203 Torr;

3-methylpentane-1,5-diol (4457-71-0) → 3-methyl-1,5-diiodopentane (51174-46-0)

Conditions	Yield
With phosphorus; iodine at 45℃; for 42h; Cooling with ice bath;	87%
With phosphorus; iodine
Multi-step reaction with 2 steps 1: 73 percent / PBr3 / 20 h / -10 - 20 °C 2: 89 percent / NaI / acetone / 3 h / Heating View Scheme

3-methylpentane-1,5-diol (4457-71-0) + p-Trifluoromethylbenzylamine (3300-51-4) → N-methyl-1-(4-(trifluoromethyl)benzyl)piperidine

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 16h; Microwave irradiation; Inert atmosphere; Sealed tube;	86%

3-methylpentane-1,5-diol (4457-71-0) → 3-methyl-1,5-dibromopentane (4457-72-1)

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 1h;	85%
With hydrogen bromide In octane; water at 147 - 148℃; for 12h; Dean-Stark;	83%
With phosphorus tribromide at -10 - 20℃; for 20h; Substitution;	73%

3-methylpentane-1,5-diol (4457-71-0) + 3-chloroprop-1-ene (107-05-1) → 1,5-Bis-allyloxy-3-methyl-pentane

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide at 40℃; for 7h;	85%

3-methylpentane-1,5-diol (4457-71-0) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-(tert-butyldimethylsilyl)oxy-3-methyl-1-pentanol (295318-34-2)

Conditions	Yield
Stage #1: 3-methylpentane-1,5-diol With n-butyllithium In tetrahydrofuran; hexane at 20℃; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃; for 0.75h; Inert atmosphere; Stage #3: With water; ammonium chloride	84%
With sodium hydride In tetrahydrofuran Substitution; Silylation;	83%
Stage #1: 3-methylpentane-1,5-diol With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃;	52%
Stage #1: 3-methylpentane-1,5-diol With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 0℃; Inert atmosphere;	51%

3-methylpentane-1,5-diol (4457-71-0) + p-toluenesulfonyl chloride (98-59-9) → 5-hydroxy-3-methylpentyl 4-methylbenzenesulfonate (1076691-71-8)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 3.16667h; Inert atmosphere;	84%

3-methylpentane-1,5-diol (4457-71-0) + 2',3',4',5',6'-pentamethylacetophenone (2040-01-9) → (4-methylcyclohex-1-en-1-yl)(2,3,4,5,6-pentamethylphenyl)methanone

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium hydroxide; catacxium A In toluene at 115℃; for 24h; Time; Sealed tube; chemoselective reaction;	84%

3-methylpentane-1,5-diol (4457-71-0) + 1,1'-(2-nitroethene-1,1-diyl)dibenzene (5670-69-9) → C34H36N2O6

Conditions	Yield
Stage #1: 3-methylpentane-1,5-diol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1,1'-(2-nitroethene-1,1-diyl)dibenzene In tetrahydrofuran at 15℃; for 15h;	82%

3-methylpentane-1,5-diol (4457-71-0) + propargyl bromide (106-96-7) → 3-methyl-1,5-bis(prop-2-yn-1-yloxy)pentane

Conditions	Yield
Stage #1: 3-methylpentane-1,5-diol With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran Inert atmosphere;	80%

3-methylpentane-1,5-diol (4457-71-0) → 3-methyl-(1,5)-azopentane

Conditions	Yield
With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 65℃; for 16h;	76%

3-methylpentane-1,5-diol (4457-71-0) + 2',3',4',5',6'-pentamethylacetophenone (2040-01-9) → (trans-4-methylcyclohexyl)(2,3,4,5,6-pentamethylphenyl)methanone

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide In toluene at 115℃; for 24h; Inert atmosphere; Sealed tube; diastereoselective reaction;	76%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide In toluene at 115℃; for 24h; Sealed tube; Inert atmosphere; diastereoselective reaction;	76%

3-methylpentane-1,5-diol (4457-71-0) + all-trans-retinoic-acid (302-79-4) → 3-methyl-1,5-diretinylpentanediester (1354766-27-0)

Conditions	Yield
Stage #1: 3-methylpentane-1,5-diol; all-trans-retinoic-acid With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 15h; Darkness; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene	74.5%

3-methylpentane-1,5-diol (4457-71-0) + triisopropylsilyl chloride (13154-24-0) → C15H34O2Si

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 5h;	70%

3-methylpentane-1,5-diol (4457-71-0) + 2-[2'-hydroxy-3'-tert-butyl-5'-(2''-methoxycarbonylethyl)phenyl]-2H-benzotriazole (84268-33-7) → C44H52N6O6

Conditions	Yield
With di(n-butyl)tin oxide at 170℃; for 20h; Dean-Stark; Inert atmosphere;	65%

3-methylpentane-1,5-diol (4457-71-0) → 2-methylbutanedioic acid (498-21-5, 636-60-2) + 3-methyl glutaric acid (626-51-7)

Conditions	Yield
With dinitrogen tetraoxide In nitric acid at 60℃; Heating;	A 62% B 23%
With dinitrogen tetraoxide In nitric acid at 50℃; Heating;	A 45% B 33%

3-methylpentane-1,5-diol (4457-71-0) → (4R)-4-methyltetrahydro-2H-pyran-2-one (61898-55-3)

Conditions	Yield
With acetate buffer pH 5 In water at 30℃; for 48h; Gluconobacter roseus IAM 1841;	57%
Multi-step reaction with 3 steps 2: Jones oxidation 3: 1.) CH2N2, 2.) aq. HCl, MeOH View Scheme

3-methylpentane-1,5-diol (4457-71-0) + p-toluenesulfonyl chloride (98-59-9) → 3-methylpentane-1,5-bis(4-methylbenzenesulfonyl)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	55%

3-methylpentane-1,5-diol (4457-71-0) + phenylcarbonochloridothioate (1005-56-7) → O-(5-hydroxy-3-methylpentyl) O-phenyl thionocarbonate (152429-69-1)

Conditions	Yield
With pyridine; dmap In acetonitrile at 0℃; for 5h;	54%

3-methylpentane-1,5-diol (4457-71-0) + 2',3',4',5',6'-pentamethylacetophenone (2040-01-9) + 3-isobutylpentane-1,1,5,5-d4-1,5-diol → (4-methylcyclohex-1-en-1-yl)(2,3,4,5,6-pentamethylphenyl)methanone + C22H29(2)H3O

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium hydroxide; catacxium A In toluene at 115℃; for 24h; Sealed tube; Overall yield = 77 percent; Overall yield = 135 mg;	A 51% B 26%

3-methylpentane-1,5-diol (4457-71-0) + acryloyl chloride (814-68-6) → 3-methyl 1,5-pentanediol diacrylate (64194-22-5)

Conditions	Yield
With triethylamine; 2-hydroxyresorcinol In benzene at 50℃; for 0.5h;	50%

Upstream product

• 38113-08-5 3,4-dihydro-2-methoxy-4-methyl-2H-pyran 
• 59677-19-9 6-methoxy-4-methyl-3,6-dihydro-2H-pyran 
• 6829-42-1 diethyl 3-methylglutarate 
• 6280-15-5 3-methylpentanedial 
• 40760-35-8 3-methylenepentane-1,5-diol 
• 626-51-7 3-methyl glutaric acid 
• 40065-27-8 1,5-diacetoxy-3-methylpentane 
• 124-41-4 sodium methylate 
• 5898-67-9 3-methyl-5-oxo-pentanoic acid methyl ester 
• 2018-45-3 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane 
• 19013-37-7 dimethyl 3-methylglutarate 
• 5164-76-1 dimethyl glutaconate 
• 763-32-6 2-methyl-1-buten-4-ol 
• 117-84-0 Di-n-octyl phthalate 

Downstream Products

• 5161-17-1 tetrahydro-4-methyl-2H-thiopyran 
• 1121-84-2 4-methyl-tetrahydro-pyran-2-one 
• 4457-72-1 3-methyl-1,5-dibromopentane 
• 2451-87-8 1,5-bis-benzoyloxy-3-methyl-pentane 
• 14446-71-0 1-benzyl-4-methylpiperidine 
• 51174-46-0 3-methyl-1,5-diiodopentane 
• 64194-22-5 3-methyl-1,5-pentanediol diacrylate 
• 61898-56-4 (S)-4-methyltetrahydro-2H-pyran-2-one 
• 626-58-4 4-methylpiperidin 
• 67512-92-9 4-methylthiane 1,1-dioxide 
• 38451-99-9 5-Methylcyclooctanon 
• 18653-57-1 4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol 

Relevant academic research and scientific papers

Method for combined production of 3-methyl-1,5-pentanediol and C1-C6 alcohols

The invention provides a method for combined production of 3-methyl-1,5-pentanediol and C1-C6 alcohols. The method comprises the following steps: 1) subjecting 3-methyl-3-butene-1-alcohol and C1-C6 acids to an esterification reaction so as to obtain an esterified product containing C1-C6 acids-3-methyl-3-butene-1-alcohol ester; 2) subjecting the esterified product obtained in the step 1) and gas containing CO and H2 to a hydroformylation reaction; and 3) subjecting a reaction product obtained in the step 2) to a hydrogenation reaction so as to obtain the 3-methyl-1,5-pentanediol and the C1-C6alcohols. According to the invention, through a process route of esterification, hydroformylation and hydrogenation in turn, direct hydroformylation of 3-methyl-3-butene-1-alcohol is avoided, so inevitable side reactions generated by a direct hydroformylation reaction is easily avoided; meanwhile, by utilization of the process route provided by the invention, combined production of the C1-C6 alcohols (like ethyl alcohol) can be realized.

METHODS OF FORMING DIOL COMPOUNDS

Methods of forming a C4 to C7 diol compound, the methods including a first step of reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a C4 to C7 lactone; and a subsequent step of reacting the lactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure, wherein the second temperature is lower than the first temperature. Also disclosed are methods of forming a solvent, the methods including reacting a C4 to C7 dicarboxylic acid with hydrogen (H2) gas on a first heterogeneous catalyst at a first temperature and a first pressure to form a solvent. Further disclosed herein are methods that include reacting mevalonolactone with hydrogen (H2) gas on a second heterogeneous catalyst at a second temperature and a second pressure to form a diol compound.

Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids

A prominent challenge in replacing petrochemical polymers with bioderived alternatives is the efficient transformation of biomass into useful monomers. In this work, we demonstrate a practical process for the synthesis of multifunctional alcohols from five- and six-carbon acids using heterogeneous catalysts in aqueous media. Design of this process was guided by thermodynamic calculations, which indicate the need for two sequential high-pressure hydrogenations: one, reduction of the acid to a lactone at high temperature; two, further reduction of the lactone to the corresponding diol or triol at low temperature. For example, the conversion of mesaconic acid into (α or β)-methyl-γ-butyrolactone was achieved with 95 % selectivity at a turnover frequency of 1.2 min?1 over Pd/C at 240 °C. Subsequent conversion of (α or β)-methyl-γ-butyrolactone into 2-methyl-1,4-butanediol was achieved with a yield of 80 % with Ru/C at 100 °C. This process is an efficient method for the production of lactones, diols, and triols, all valuable monomers for the synthesis of bioderived branched polyesters.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

PROCESS FOR PRODUCING POLYHYDRIC ALCOHOL

A process for producing a polyhydric alcohol includes a step (I) of hydrogenating hemiacetal having a specific structure to obtain a reaction solution (I), and a step (II) of adding water to the reaction solution (I) obtained in the step (I) and further conducting hydrogenation.

Process for producing polyhydric alcohol

A process for producing a polyhydric alcohol which comprises a step (I) in which a hemiacetal having a specific structure is hydrogenated to obtain a liquid reaction mixture (I) and a step (II) in which water is added to the liquid reaction mixture (I) obtained in the step (I) to further conduct hydrogenation.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

METHOD FOR PRODUCTION OF 3-METHYL-1,5-PENTANEDIOL

Provided is a method for producing 3-methyl-1,5-pentanediol by hydrogenating 2-hydroxy-4-methyltetrahydropyran in the presence of a hydrogenation catalyst, characterized in that the hydrogenation is further carried out in the presence of a basic compound. By this method, in producing MPD by hydrogenation of MHP, high-purity MPD can be produced by effectively suppressing generation of by-products such as MPAE and MVL even when a known hydrogenation catalyst is used.

METHOD FOR PRODUCING 3-METHYL-1,5-PENTANEDIOL

Provided is a method for producing 3-methyl-1,5-pentanediol by hydrogenating 2-hydroxy-4-methyltetrahydropyran in the presence of a hydrogenation catalyst, characterized in that the hydrogenation is further carried out in the presence of a basic compound. By this method, in producing MPD by hydrogenation of MHP, high-purity MPD can be produced by effectively suppressing generation of by-products such as MPAE and MVL even when a known hydrogenation catalyst is used.

Design, synthesis, and antipicornavirus activity of 1-[5-(4-arylphenoxy) alkyl]-3-pyridin-4-ylimidazolidin-2-one derivatives

A series of pyridylimidazolidinone derivatives was synthesized and tested in vitro against enterovirus 71 (EV71). On the basis of compound 33 (DBPR103), introduction of a methyl group at the 2- or 3-position of the linker between the imidazolidinone and the biphenyl resulted in markedly improved antiviral activity toward EV71 with IC50 values of 5.0 nM (24b) and 9.3 nM (14a), respectively. Increasing the branched chain to propyl resulted in a progressive decrease in activity, while inserting different heteroatoms entirely rendered the compound only weakly active. The introduction of a bulky group (cyclohexyl, phenyl, or benzyl) led to loss of activity against EV71. The 4-chlorophenyl moiety in 14a was replaced with bioisosteric groups such as oxadiazole (28a-d) or tetrazole (32a,b), dramatically improving anti-EV71 activity and selectivity indices. Compounds 14a, 24b, 28b, 28d, and 32a exhibited a strong activity against lethal EV71, and no apparent cellular toxicity was observed. Three of the more potent imidazolidinone compounds, 14a, 28b, and 32b, were subjected to a large group of picornaviruses to determine their spectrum of antiviral activity.