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[ CAS No. 5464-28-8 ] {[proInfo.proName]}

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Chemical Structure| 5464-28-8
Chemical Structure| 5464-28-8
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Product Details of [ 5464-28-8 ]

CAS No. :5464-28-8 MDL No. :MFCD00003218
Formula : C4H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BOHGAOWOIJMTPZ-UHFFFAOYSA-N
M.W : 104.10 Pubchem ID :21618
Synonyms :

Calculated chemistry of [ 5464-28-8 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 22.56
TPSA : 38.69 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : -4.74
Log Po/w (WLOGP) : -0.65
Log Po/w (MLOGP) : -1.05
Log Po/w (SILICOS-IT) : 0.54
Consensus Log Po/w : -0.9

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 2.57
Solubility : 38400.0 mg/ml ; 369.0 mol/l
Class : Highly soluble
Log S (Ali) : 4.56
Solubility : 3740000.0 mg/ml ; 35900.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.28
Solubility : 199.0 mg/ml ; 1.91 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.89

Safety of [ 5464-28-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5464-28-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5464-28-8 ]

[ 5464-28-8 ] Synthesis Path-Downstream   1~72

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YieldReaction ConditionsOperation in experiment
95.6% With dihydrogen peroxide; nitric acid; cetyltrimethylammonim bromide; ferric nitrate; In water; at 80℃; for 5.0h; Will be 920g of glycerin,990gParaformaldehyde and20 g of the supported solid super acid catalyst prepared in Example 2 was addedIn the reaction device, the reaction is heated to 80 ° C, and the water having a lower boiling point and the trioxane formed in the reaction process enters the fractionation device.According to the principle that the boiling point of paraformaldehyde is lower than water, the triacetal is fractionated back to the reaction unit through a fractionation device.The reaction was carried out as a raw material, and the reaction was completed for 5 hours to obtain glycerol formal, and the product was analyzed by HPLC-MS.At 96.3percent, the ratio of the six-membered ring product to the product of the five-membered ring in the product was 70:25.
With Dowex 50; In toluene; at 100℃;Dean-Stark; Reflux; A 250 mL three neck flask equipped with a stirrer, an addition funnel, and a Dean-Stark trap was charged with glycerol (9.2 g, 0.1 mol), paraformaldehyde (2.7 g, 0.09 mol), activated ion exchange resin Dowex 50 (10 wt.%), and anhydrous toluene (70 mL). The reaction mixture was refluxed until calculated amount of water was distilled off. The mixture was cooled and filtered. The solvent was removed in low vacuum. Distillation of the residue afforded a mixture of compounds 1a and 1b in the yield of 9.2 g (93%), b.p. 190-195 C (760 Torr). An isomeric ratio was determined by 1H NMR spectroscopy from the integrated intensity ratio of the signals of H(4) methyne protons (deltaH 3.5-4.0) of dioxolane 1a and H(5) methyne proton (deltaH 3.5-4.0) of dioxane 1b. Compound 1a. MS (EI, 70 eV), m/z (Irel (%)): 103 [M - H]+ (not detected), 73 (75), 57 (15), 45 (100), 31 (15). Compound 1b. MS (EI, 70 eV), m/z (Irel (%)): 103 [M - H]+ (not detected), 87 (1), 74 (31), 45 (17), 44 (100), 31 (12).
With 1,3,5-Trioxan; at 80℃; for 5.0h; 920 g of glycerin, 990 g of trioxane and 20 g of the supported solid superacid catalyst prepared in Example 2 were charged into a reaction apparatus, and heated to 80 ° C to react, and the lower boiling water and trioxane formed during the reaction were fractionated. The device, according to the principle that the boiling point of the paraformaldehyde is lower than water, the triacetal is fractionated back to the reaction device through the fractionation device to continue the reaction as a raw material, and the reaction is finished for 5 hours, thereby obtaining glycerol formal, which is analyzed by HPLC-MS. The yield of the product was 93.5percent, and the ratio of the product of the six-membered ring product to the product of the five-membered ring was 77:23.
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YieldReaction ConditionsOperation in experiment
95% With Amberlyst 15 resin acid catalyst; at 100℃; for 5.0h;Large scale; Green chemistry; 1000 g of glycerin (analytical grade) was taken, added to a 1000 mL three-necked flask, and the temperature was raised to 100 C, and 260-400 g of paraformaldehyde was added in portions.After all the paraformaldehyde was dissolved, 20% of the A15 resin acid catalyst (based on the mass of glycerin) was added.Keep the three-necked bottle open,The reaction was continued for five hours while maintaining 100 C.After cooling to 40 C, it was suction filtered with a Buchner funnel.Sodium carbonate was added to the flask to neutralize to pH 7, and the solid impurities were removed after standing.The filtrate was separated by a rotary evaporator. Remove the water before 40-50C, then heat to 70-80C to distill off the first fraction (by-product), then slowly increase to 130-150C to collect the second fraction, ie, glycerol formal (colorless, transparent, liquid with a certain viscosity) ) 1118 grams,The yield is over 95% (calculated as glycerol).
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  • [ 106-89-8 ]
  • [ 13014-80-7 ]
YieldReaction ConditionsOperation in experiment
With tetrabutyl-ammonium chloride; potassium penicillin V; Example 2 Commercial glycerol formal is separated in its two isomers (4-hydroxymethyl-1,3-dioxolane and 5-hydroxy-1,3-dioxane) according to the method of Hibbert et al. [J. Am. Chem. Soc. 50, 3120 (1928)]. To 10.4 g of 4-hydroxymethyl-1,3-dioxolane (isomer 1) are added under vigorous agitation 5.8 g of KOH grounded in a mixer, 200 mg of tetrabutylammonium chloride acting as a phase transfer catalyst. 9.2 g of epichlorhydrin are then added progressively to allow the temperature to remain below 30° C. by external cooling. KCl formed is separated by filtration and the (4-glycidoxymethyl)-1,3-dioxolane obtained is purified through two distillations. This monomer is copolymerized with ethylene oxide in the conditions of example 12 by using potassium tert-butoxide as the anionic initiator.
  • 38
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  • [ 50270-99-0 ]
  • 4-(α-D-glucopyranosyl)oxymethyl-1,3-dioxolane [ No CAS ]
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  • [ 371-27-7 ]
  • Butyric acid (S)-1-[1,3]dioxolan-4-ylmethyl ester [ No CAS ]
  • Butyric acid (R)-1-[1,3]dioxolan-4-ylmethyl ester [ No CAS ]
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  • 1,2-O-methyleneglycerol 3-(diethyl phosphate) [ No CAS ]
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  • [ 2283-11-6 ]
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  • [ 98238-47-2 ]
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  • (+-)-4-<chloromethoxy-methyl>-<1,3>dioxolane [ No CAS ]
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  • [ 56-81-5 ]
  • (HCHO)n [ No CAS ]
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  • [ 7647-01-0 ]
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  • polyoxymethylene [ No CAS ]
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  • polyoxymethylene [ No CAS ]
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  • [ 1012073-06-1 ]
  • C9H13N3O4S2 [ No CAS ]
  • C9H13N3O4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 2.0h; Example 14 and Example 15; In 2 ml of tetrahydrofuran were dissolved 224 mg of <n="183"/>the compound represented by the formula (IIa-1) and 125 mg of <strong>[4740-78-7]glycerol formal</strong>, 50 mg of sodium hydride was added under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Thereafter, an aqueous saturated ammonium chloride was added to the reaction mixture, followed by extraction with t-butyl methyl ether. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was subjected to medium pressure preparative liquid chromatography to obtain 67 mg of a compound represented by the formula (14) :(hereinafter, referred to as present compound (14)) and 74 mg of a compound represented by the formula (15) :(hereinafter, referred to as present compound (15) . Present compound (14)1H-NMR (CDCl3, TMS) delta (ppm) : 5.07 (IH, s) , 4.93 (IH, s), 4.59 (2H, m) , 4.47 (IH, m) , 4.04 (IH, dd) , 3.79 (IH, dd) , '3.04 (6H, br)Present compound (15)1H-NMR (CDCl3, TMS) delta (ppm): 5.06 (IH, m) , 5.03 (IH, d) , <n="184"/>4.83 (IH, d) , 4.26 (2H, dd) , 4.08 (2H, dd) , 3.04 (6H, br)
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  • [ 1012073-07-2 ]
  • C11H15N3O5S2 [ No CAS ]
  • C11H15N3O5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 2.0h; Example 129 and, Example 130; In 2 ml of tetrahydrofuran were dissolved 532 mg of a 'compound represented by the formula (IIa-2) and 230 mg of <strong>[4740-78-7]glycerol formal</strong>, 100 mg of sodium hydride (60percent oily) was added under ice-cooling, and the mixture was stirred at <n="242"/>room temperature for 2 hours. Thereafter, an aqueous saturated ammonium chloride solution was added to the reaction mixture, followed by extraction with t-butyl methyl ether. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was subjected to medium pressure preparative liquid chromatography to obtain 210 mg of a compound represented by the formula (129) :(hereinafter, referred to as present compound (129)) and 204 mg a compound represented by the formula (130) :(hereinafter, referred to as present compound (130)) .Present compound (129) 1H-NMR (CDCl3, TMS) delta (ppm) : 5.07 (IH, s), 4.93 (IH, s),4.59 (2H, m) , 4.47 (IH, m) , 4.04 (IH, dd) , 3.80 (IH, dd) ,3.72 (4H, t) , 3.57 (4H, s)Present compound (130)'1H-NMR (CDCl3, TMS) delta (ppm): 5.06 (IH, m) , 5.03 (IH, d) , 4.83 (IH, d) , 4.25 (2H, dd) , 4.08 (2H, dd) , 3.72 (4H, t) ,3.56 (4H, s)
  • 52
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  • [ 54562-14-0 ]
  • 5-(γ-linolenoyloxy)-1,3-dioxan [ No CAS ]
  • [ 909000-55-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichloromethane; at 5 - 20℃; for 2.16667h; EXAMPLE 2.; 2-GLA <strong>[4740-78-7]glycerol formal</strong> (aka: 5-y-linolenoyloxy)-l,3-dioxan and 5-d,3-dioxanvD- methyl-gamma-linolenate); For the purposes of this exemplification, the synthesis of this ester was carried out by acylation of the commercially available <strong>[4740-78-7]glycerol formal</strong> mixture using gamma-linolenoyl chloride. By this method a mixture of two products is formed and these were separable by column chromatography. The undesired by-product is eluted off the column first; further elution gives the desired acetal-ester. It is a yellow oil at room temperature and appears to have stability properties similar to GLA, stable in air at room temperature for short periods (days) but is best stored long term in a cool place under nitrogen.ExperimentalOxalyl chloride (2.6 ml, 3.78 g, 30 mmol, 1.5 equiv) was added to a solution of gamma- linolenic acid (GLA, 5.56 g, 20 mmol. 1.0 equiv) in dichloromethane (DCM, 40 ml). The resulting solution was stirred under N2 at room temperature overnight and then concentrated in vacuo. The residual oily gamma-linolenoyl chloride was added dropwise EPO <DP n="17"/>over 10 min to a stirred solution of <strong>[4740-78-7]glycerol formal</strong> (2.50 g, 24 mmol, 1.2 equiv) in DCM (40 ml) containing pyridine (10 ml, 9.78 g, 0.12 mol, 6 equiv) at 5 0C. The reaction mixture was stirred at room temperature for 2h, the precipitated pyridine hydrochloride filtered off, and the filtrate washed with water (2 x ). After drying over MgSO4 the solvent was removed in vacuo to give a light tan oil (6.5 g). This material was chromatographed on silica (60 g). Elution with hexane-ether (94:6) gave 5.2 g of an oil consisting of two components (TLC, HPLC). These were separated on a second silica column (6Og). Elution with hexane-ether (98:2 then 95:5) gave 4-(gamma- linolenoyloxymethyl)- 1,3-dioxolane as a yellow oil (1.2 g, 98percent by HPLC). deltaH (500 MHz, CDCl3) 0.89 (3H, t, J= 7.0 Hz, CH3), 1.24-1.45 (8H, complex m, 4 x CH2), 1.65 (2H, p, J= 7.5 Hz5 CH2-C-CO), 2.08 (4H1 m, 2 x CH2C=C), 2.35 (2H3 1, J = 7.5 Hz, CH2CO), 2.80 (4H, t, J = 6.0 Hz, 2 x C=CCH2C=C), 3.67 (IH, m, OCITLambdaHB), 3.97 (IH, m, OCHAi2s), 4.14 (2H5 m, OCHAHB), 4.26 (IH, p, J= 3.5 Hz5 CHO)5 4.89 and 5.02 (2H, 2 x s, OCH2O)5 5.36 (6H, m, 3 x CH=CH). deltac (126.8 MHz, CDCl3) 14.09 (CH3), 22.60, 24.51, 25.65, 26.85, 27.23, 29.16, 29.34, 31.53, 33.97, 63.93 (CH2O), 66.72 (CH2O), 73.31 (CHO)5 95.44 (OCO), [127.60, 128.04, 128.32, 128.41, 129.50, 130.41, olefmic C], 173.26 (carbonyl).Further elution gave 5-(gamma-linolenoyloxy)-l,3-dioxan as a yellow oil (1.6 g, 97.8percent) by HPLC). deltaH (500 MHz, CDCl3) 0.89 (3H, t, J= 7.0 Hz, CH3), 1.24-1.46 (8H, complex m, 4 x CH2), 1.67 (2H5 p, J = 7.5 Hz, CH2-C-CO)5 2.05 (4H5 m, 2 x CH2C=C), 2.40 (2H, t, J = 7.5 Hz, CH2CO), 2.81 (4H, t, J = 6.0 Hz, 2 x C=CCH2C=C)5 3.91 (2H5 m, OCH2), 3.99 (2H5 m, OCH2), 4.73 (IH5 p, J= 3.5 Hz5 CHO)5 4.80 (IH, d, J = 6.0 Hz, OCHAHBO), 4.93 (IH, d, J = 6.0 Hz, OCHANo.*O), 5.37 (6H5 m, 3 x CH=CH). deltac (126.8 MHz5 CDCl3) 14.08 (CH3), 22.59, 24.53, 25.65, 26.86, 27.22, 29.06, 29.34, 31.52, 34.12, 65.54 (CHO), 68.55 (CH2O), 93.66 (OCO), [127.60, 128.05, 128.32, 128.42, 129.51, 130.42, olefmic C]5 173.12 (carbonyl). Some fractions containing both compounds were obtained during the chromatography and these could be recycled if necessary to give more material. The reaction scheme for this synthesis is shown in the figures below.
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YieldReaction ConditionsOperation in experiment
With hydrogenchloride; In pyridine; di-isopropyl ether; glycerol; PREPARATION H 1,3-Dioxacyclohex-5-yl p-Toluenesulfonate p-Toluenesulfonyl chloride (38.1 g, 0.2 mole) was added to a solution of 20.8 g (0.2 mole) <strong>[4740-78-7]glycerol formal</strong> (a mixture comprised of 67percent 1,3-dioxan-5-ol and 33percent (1,3-dioxolan-4-yl)methanol) in 200 ml. pyridine cooled to 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 1/2 hr., then at 25° C. for 20 hr. The mixture was added to 500 ml. 6N aqueous hydrochloric acid solution and the resulting mixture was extracted with four 200 ml. portions of ethyl acetate. The combined ethyl acetate extracts were washed with two 200 ml. portions of lN aqueous hydrochloric acid solution, two 200 ml. portions of water and 200 ml. saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. The crude product was dissolved in 500 ml. di-isopropyl ether whereupon the desired 1,3-dioxacyclohex-5-yl tosylate crystallized. Filtration yielded 17.4 g of white crystalline tosylate, m.p. 91°-92° C. Another 4.3 g of crystalline tosylate was obtained from the mother liquors (total yield 42percent). The NMR spectrum of the title compound as a deuterochloroform solution had peaks at 2.45 (s,3H); 3.54-4.13 (c,4H); 4.26-4.6 (m,1H), 4.75 (s,2H); 7.3 (d,2H); and 7.8 (d, 2H) ppm.
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  • [ 116-14-3 ]
  • 4-(1,1,2,2-tetrafluoroethoxy)methyl-2,2-dimethyl-1,3-dioxolane [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; EXAMPLE 10 Preparation of 4-(1,1,2,2-tetrafluoroethoxy)methyl-2,2-dimethyl-1,3-dioxolane. Sodium hydride (0.91 g in suspension in oil at 50percent) is added to the solution of 4-hydroxymethyl-1,3-dioxolane (5 g) in anhydrous DMF (70 ml), at 0° C., under nitrogen. The temperature is then allowed to rise back to room temperature and the reaction mixture is stirred for 30 minutes. After evacuating the reaction equipment, perfluoroethylene is added; the whole is left standing under an atmosphere of this gas for 20 hours, the exothermic heat initially evolved being absorbed, so to avoid a temperature increase. The reaction mixture is then poured into water, and extracted with ethyl ether; the ether extract is washed with water, dried over sodium sulphate and evaporated to dryness. An orange-coloured oil is obtained (5 g), which is used as such for the reaction according to Example 9.
In N,N-dimethyl-formamide; Example 10 Preparation of 4-(1,1,2,2-tetrafluoroethoxy)-methyl-2,2-dimethyl-1,3-dioxolane. Sodium hydride (0.91 g in suspension in oil at 50percent) is added to the solution of 4-hydroxymethyl-1,3-dioxolane (5 g) in anhydrous DMF (70 ml), at 0°C, under nitrogen. The temperature is then allowed to rise back to room temperature and the reaction mixture is stirred for 30 minutes. After evacuating the reaction equipment, perfluoroethylene is added; the whole is left standing under an atmosphere of this gas for 20 hours, the exothermic heat initially evolved being absorbed, so to avoid a temperature increase. The reaction mixture is then poured into water, and extracted with ethyl ether; the ether extract is washed with water, dried over sodium sulphate and evaporated to dryness. An orange-coloured oil is obtained (5 g), which is used as such for the reaction according to Example 9. I.R. (cmmin1): 1270, 1210, 1120, 1090. 1H N.M.R.(60 MHz) TMS in CCl4. delta: 1.35 (s, 3H); 1.40 (s, 3H); 3.65-4.50 (m, 5H); 5.75 (tt, 1H).
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  • 1,3-dioxan-5-yl 2-oxiranylmethyl ether [ No CAS ]
  • [ 13014-80-7 ]
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  • [ 3282-30-2 ]
  • [ 1404077-71-9 ]
  • 2,2-Dimethyl-propionic acid [1,3]dioxolan-4-ylmethyl ester [ No CAS ]
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  • [ 1404077-71-9 ]
  • 2,2-Dimethyl-propionic acid [1,3]dioxolan-4-ylmethyl ester [ No CAS ]
  • [ 5464-28-8 ]
  • [ 4740-78-7 ]
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  • [ 96-26-4 ]
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  • C9H16O6 [ No CAS ]
  • C8H14O6 [ No CAS ]
  • C7H12O6 [ No CAS ]
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  • [ 124-07-2 ]
  • (1,3-dioxolan-4-yl)methyl octanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With toluene-4-sulfonic acid; In neat (no solvent); at 60℃; for 4.0h; General procedure: The FFA (2.0 g), glycerol formal (GlyF: 1.5 molar equivalent respect to the FFA) andp-toluene-sulfonic acid (5percent w/w respect of the weight of the FFA) were charged in a conventionalround bottom flask with a magnetic stirrer. The mixture was heated at 60 C and stirred vigorously for4 h. The reaction was quenched by neutralizing the acid catalyst with saturated solution of sodiumcarbonate then filtered. The liquid phase was collected in a separatory funnel and partitioned betweenchloroform and water (3 x 20 mL). The organic layer was dried over sodium sulfate, filtered and thesolvent eliminated using a rotary evaporator. The sample was stored in a glass vial Table 2 summarizesthe experimental conditions and the results of reactions between GlyF and the FFAs. (1,3-Dioxolan-4-yl)methyl octanoate (5) Liquid at RT; 1H-NMR (400 MHz, CDCl3) delta 4.35?3.41 (m, 4H),2.35 (ddd, J = 9.8, 6.6, 2.2 Hz, 2H), 1.63 (depth, J = 11.1, 3.5 Hz, 2H), 1.44 (s, 2H), 1.29 (d, J = 6.0 Hz, 9H),0.92?0.85 (m, 3H); 13C-NMR (100 MHz) delta 178.88, 95.12, 77.38, 68.26, 63.03, 33.95, 33.84, 31.32, 28.75,28.72, 28.58, 24.57, 24.39, 22.27, 13.73; GC-MS (relative intensity, 70 eV) m/z: 69 (5), 83 (5), 116 (5), 84 (6),109 (7), 42 (8), 58 (8), 73 (8), 126 (8), 128 (8), 98 (9), 103 (10), 45 (11), 87 (11), 145 (12), 146 (15), 41 (21),43 (21), 55 (26), 86 (68), 57 (77), 127 (100), 230 ([M]+, <1percent); IR (wavenumber cm-1; Transmittance percent)3558; 77, 2930; 32, 2858; 44, 1739; 32, 1492; 68, 1384; 61, 1166; 44, 1045; 55, 942; 64,757; 56.
  • 67
  • [ 5464-28-8 ]
  • [ 143-07-7 ]
  • (1,3-dioxolan-4-yl)methyl dodecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With toluene-4-sulfonic acid; In neat (no solvent); at 60℃; for 4.0h; General procedure: The FFA (2.0 g), glycerol formal (GlyF: 1.5 molar equivalent respect to the FFA) andp-toluene-sulfonic acid (5percent w/w respect of the weight of the FFA) were charged in a conventionalround bottom flask with a magnetic stirrer. The mixture was heated at 60 C and stirred vigorously for4 h. The reaction was quenched by neutralizing the acid catalyst with saturated solution of sodiumcarbonate then filtered. The liquid phase was collected in a separatory funnel and partitioned betweenchloroform and water (3 x 20 mL). The organic layer was dried over sodium sulfate, filtered and thesolvent eliminated using a rotary evaporator. The sample was stored in a glass vial Table 2 summarizesthe experimental conditions and the results of reactions between GlyF and the FFAs.
  • 68
  • [ 5464-28-8 ]
  • [ 57-10-3 ]
  • (1,3-dioxolan-4-yl)methyl palmitate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With toluene-4-sulfonic acid; In neat (no solvent); at 60℃; for 4.0h; General procedure: The FFA (2.0 g), glycerol formal (GlyF: 1.5 molar equivalent respect to the FFA) andp-toluene-sulfonic acid (5percent w/w respect of the weight of the FFA) were charged in a conventionalround bottom flask with a magnetic stirrer. The mixture was heated at 60 C and stirred vigorously for4 h. The reaction was quenched by neutralizing the acid catalyst with saturated solution of sodiumcarbonate then filtered. The liquid phase was collected in a separatory funnel and partitioned betweenchloroform and water (3 x 20 mL). The organic layer was dried over sodium sulfate, filtered and thesolvent eliminated using a rotary evaporator. The sample was stored in a glass vial Table 2 summarizesthe experimental conditions and the results of reactions between GlyF and the FFAs.
  • 69
  • [ 5464-28-8 ]
  • [ 57-11-4 ]
  • (1,3-dioxolan-4-yl)methyl stearate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With toluene-4-sulfonic acid; In neat (no solvent); at 60℃; for 4.0h; General procedure: The FFA (2.0 g), glycerol formal (GlyF: 1.5 molar equivalent respect to the FFA) andp-toluene-sulfonic acid (5percent w/w respect of the weight of the FFA) were charged in a conventionalround bottom flask with a magnetic stirrer. The mixture was heated at 60 C and stirred vigorously for4 h. The reaction was quenched by neutralizing the acid catalyst with saturated solution of sodiumcarbonate then filtered. The liquid phase was collected in a separatory funnel and partitioned betweenchloroform and water (3 x 20 mL). The organic layer was dried over sodium sulfate, filtered and thesolvent eliminated using a rotary evaporator. The sample was stored in a glass vial Table 2 summarizesthe experimental conditions and the results of reactions between GlyF and the FFAs.
  • 70
  • [ 56-81-5 ]
  • [ 5464-28-8 ]
  • [ 4740-78-7 ]
  • [ 79-14-1 ]
  • [ 623-50-7 ]
  • [ 627-82-7 ]
  • [ 556-52-5 ]
  • [ 116-09-6 ]
  • [ 107-02-8 ]
YieldReaction ConditionsOperation in experiment
62% With pretreated aluminium vanadium phosphate; In water; at 280℃; under 760.051 Torr;Catalytic behavior; Activation energy; The glycerol transformation was carried out in a continuous-flow fixed-bed reactor under atmospheric pressure, as previouslydescribed [23]. The reactor was made of stainless-steel tubing(7 mm internal diameter and 190 mm long), placed in a tubularelectric furnace. The temperature was monitored by a thermocou-ple located in the catalyst bed. The analysis of the feed and reactionproducts was carried out on-line using a multicolumn gas chro-matograph (GC) equipped with both flame ionization (FID) andthermal conductivity (TCD) detectors in parallel. The compoundswere separated in a capillary column, DB-1 (100percent methylpolysilox-ane, 60 m x 0,25 mm x 0,25 m).The catalyst (100 mg) was pretreated at the reaction tempera-ture during 2 h in a N2flow (75 mL/min). A 36 wtpercent glycerol (99.5percent,Sigma-Aldrich) aqueous solution was fed at 0.6 mL/h (0.69 mol/sof glycerol). In general, each catalytic test was conducted at least for3 h at different temperatures (220C, 250C and 280C). The reac-tion products were identified by chromatographic patterns and/or agas chromatograph-mass spectrometer (GC?MS) (VARIAN CP 3800,QUADRUPOLE MS 1200) also equipped with a capillary column DB-1. A blank test showed the absence of homogeneous reactions andthe reactor inactivity in the absence of a catalyst.
  • 71
  • [ 5464-28-8 ]
  • [ 115-11-7 ]
  • C8H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With Amberlyst 15 resin acid catalyst; at 70℃; for 8.0h;Inert atmosphere; Green chemistry; The above glycerol formal is added to a 5 L reaction kettle, and an A15 resin acid catalyst (10% by mass of glycerol formal) is added to the kettle, and isobutylene (3 equivalents, equivalent to glycerol formal) is introduced. And pass a certain amount of nitrogen.The stirring was started, the temperature was raised to 70 C, and the reaction was carried out at this temperature for 8 hours. The reaction was stopped and the mixture was cooled to room temperature to recover isobutylene. The catalyst was removed by filtration and the pH was adjusted to 7. Distillation under reduced pressure gave the product A in a yield of 84%.
  • 72
  • [ 5464-28-8 ]
  • (1,3-dioxolan-4-yl)methyl 1,3-dioxolane-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With 3,5-Lutidine; trichloroisocyanuric acid; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical; In acetonitrile; at -10 - 10℃; for 3.0h;Inert atmosphere; General procedure: In a 50-mL flask equipped with a 20-mL dropping funnel, 3.19 g of a mixture of 1,3-dioxan-5-ol and 4-hydroxymethyl-1,3-dioxolane (a trade name: Glycerol Formal, manufactured by Tokyo Chemical Industry Co., Ltd., purity: 98.0%, 30.0 mmol; Reference Literature 1 (Journal of Catalysis, Vol. 245, pp.428-435, 2007) describes 1H-NMR signal assignment of a proton at the 2-position of two kinds of isomers, and an isomer ratio of 1,3-dioxan-5-ol to 4-hydroxymethyl-1,3-dioxolane determined from this information and the 1H-NMR analysis was 58/42), 4.7 mg of 2-hydroxy-2-azaadamantane (AZADOL, a trademark, manufactured by Nissan Chemical Corporation, purity: 98.0%, 30 mumol), 4.92 g of 3,5-lutidine (purity: 98.0%, 45.0 mmol), and 10 g of 2-butanone were charged and stirred in a nitrogen atmosphere while cooling. A solution of 2.94 g of TCCA (purity: 95.0%, 12.0 mmol) dissolved in 10 g of 2-butanone was charged in the dropping funnel and dropped over 1 hour while regulating a dropping rate such that the reaction solution temperature within the flask fell within a range of from -10 C. to 10 C. The cooling was stopped, and the stirring was further continued for 2 hours while raising the reaction solution temperature to around 25 C. Finally, 0.20 g of 2-propanol (purity: 99.7%, 3.3 mmol) was added, and the stirring was further performed for 10 minutes, thereby completing the reaction. After filtering off a by-produced powdered solid, the filtrate was subjected to GC analysis. As a result, the conversion of 4-hydroxymethyl-1,3-dioxolane was 100%, the yield of (1,3-dioxolan-4-yl)methyl 1,3-dioxolane-4-carboxylate was 91%, and the recovery of the unreacted 3,5-lutidine relative to the charged amount was 18%. (0162) In a stirred mixed liquid of 50 g of tert-butyl methyl ether having the whole amount of the filtration residue dispersed therein and 25 g of ion exchanged water, a 2 mol/L sodium hydroxide aqueous solution was dropped until the pH of the water layer became 12 or more. At the time of completion of dropping, the filtration residue was dissolved in oily water. As a result of GC analysis of the tert-butyl methyl ether solution from which the water layer had been removed through oil-water separation, the recovery of the 3,5-lutidine relative to the charged amount was 76%, and a total recovery was 94%.
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