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Product Details of [ 6920-24-7 ]

CAS No. :6920-24-7 MDL No. :MFCD00004727
Formula : C16H34O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BTOOAFQCTJZDRC-UHFFFAOYSA-N
M.W : 258.44 Pubchem ID :98037
Synonyms :
Chemical Name :Hexadecane-1,2-diol

Safety of [ 6920-24-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6920-24-7 ]

* 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 [ 6920-24-7 ]

[ 6920-24-7 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 629-73-2 ]
  • [ 6920-24-7 ]
YieldReaction ConditionsOperation in experiment
With osmium(VIII) oxide; dihydrogen peroxide; <i>tert</i>-butyl alcohol und folgende Verseifung;
With formic acid; dihydrogen peroxide at 40℃; und folgende Verseifung;
With dihydrogen peroxide; acetic acid at 95℃; und folgende Verseifung;
With iodine; silver benzoate; benzene zuletzt bei Siedetemperatur und Verseifen des entstandenen Dibenzoats mit siedender wss.-alkoh.KOH;
mit Hilfe von Candida lipolytica; levorotatory substance;
(oxidation);
With benzenesulfonamide; potassium osmate(VI) dihydrate; (DHQD)2PHAL; potassium carbonate; potassium hexacyanoferrate(III) In water; <i>tert</i>-butyl alcohol at 20℃;
With osmium(VIII) oxide In diethyl ether; water; <i>tert</i>-butyl alcohol at 20℃; for 0.5h; Inert atmosphere;
With osmium(VIII) oxide; dihydrogen peroxide; <i>tert</i>-butyl alcohol und folgende Verseifung;
With air; boric acid in Fettsaeuren (C6-C9) und folgende Verseifung;

  • 2
  • [ 34297-27-3 ]
  • [ 6065-82-3 ]
  • [ 6920-24-7 ]
  • 5,5-dimethyl-thiazolidine-2,4-dicarboxylic acid-2-ethyl ester-4-methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate dextrorotatory substance;
  • 3
  • [ 6920-24-7 ]
  • [ 79-11-8 ]
  • [ 56741-58-3 ]
YieldReaction ConditionsOperation in experiment
63% With potassium In <i>tert</i>-butyl alcohol for 48h; Heating;
(i) K, tBuOH, (ii) /BRN= 605438/; Multistep reaction;
  • 4
  • [ 7320-37-8 ]
  • [ 1068-90-2 ]
  • [ 6920-24-7 ]
  • 3-Acetylamino-2-oxo-5-tetradecyl-tetrahydro-furan-3-carboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With potassium <i>tert</i>-butylate; Aliquat 336; lithium chloride In tetrahydrofuran at 120℃; for 18h;
  • 5
  • [ 7320-37-8 ]
  • [ 6920-24-7 ]
YieldReaction ConditionsOperation in experiment
With Aliquat 336; potassium carbonate; 2-acetylaminomalonic acid diethyl ester; lithium chloride In tetrahydrofuran at 120℃; for 18h;
  • 6
  • [ 3884-71-7 ]
  • [ 6920-24-7 ]
  • [ 114838-54-9 ]
YieldReaction ConditionsOperation in experiment
91%
  • 7
  • [ 6920-24-7 ]
  • [ 2765-11-9 ]
YieldReaction ConditionsOperation in experiment
89% With sodium periodate for 6h; Inert atmosphere;
96 % Spectr. With periodate form of Amberlite IRA 904 In dichloromethane for 3h; Heating;
  • 8
  • [ 6920-24-7 ]
  • [ 106-95-6 ]
  • [ 151331-30-5 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: hexadecane-1,2-diol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: allyl bromide In tetrahydrofuran for 22h; Heating; Further stages.;
16.5% With sodium hydride In N,N-dimethyl-formamide 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h;
With sodium hydride 1) THF, 45 deg C, 30 min; 2) THF, 45 deg C, 20 h; Yield given. Multistep reaction;
  • 9
  • [ 6920-24-7 ]
  • [ 76-83-5 ]
  • [ 39033-25-5 ]
YieldReaction ConditionsOperation in experiment
73.8% With pyridine at 60℃; for 12h;
  • 10
  • [ 6920-24-7 ]
  • 4-Tetradecyl-[1,3,2]dioxathiolane 2-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In tetrachloromethane for 0.5h; Heating;
YieldReaction ConditionsOperation in experiment
Stage #1: iron(III)-acetylacetonate; hexadecane-1,2-diol; (Z)-9-octadecen-1-amine; cis-Octadecenoic acid In diphenylether at 265℃; for 0.5h; Stage #2: iron(III) chloride; 3β-[N-(N',N'-dimethylaminoethane)carbamoyl]cholesterol hydrochloride; iron(II) chloride With ammonia; water In chloroform sonication; 4 Cholesterol-coated iron oxide particles a (the emulsion method performed at low temperature) [00160] Two water-phase solutions, one containing an iron precursor in water, the other a base solution OfH2O with 10% NH4OH, were prepared. The water-phase solution with an iron precursor contained a mixture solution OfFeCl3-OH2O (0.75 g) and FeCl2.4H2O (0.32 g) in 10 ml of water. Then, 20 μl of each of the above "water phase" solutions was added to 2 cc of the "oil phase", which is chloroform containing 0.2% Cholesteryl 3β-N-(dimethylaminoethyl)carbamate hydrochloride. Both mixtures were separately sonicated to obtain emulsions. The two emulsions were then mixed together, and dried in nitrogen for 1 hr. After that, chloroform was added again to re-suspend the emulsion. Large particles were then removed by centrifugation at 5,000 rpm for 20 min. The supernatant was again centrifuged at 7,000 rpm for 30 min to collect particles, whereas the supernatant that contained free cholesterol was discarded. The collected particles were re-suspended in chloroform to obtain a suspension of oily dark -brown cholesterol-coated iron oxide particles.
  • 13
  • [ 6920-24-7 ]
  • [ 2530-30-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Et3N 2: dimethylformamide 3: H2SO4
  • 14
  • [ 6920-24-7 ]
  • [ 151331-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: NaH / tetrahydrofuran / 1 h / 20 °C 1.2: 82 percent / tetrahydrofuran / 22 h / Heating 2.1: NaBH4; BF3*OEt2 / tetrahydrofuran / 20 h / 0 °C 2.2: 24 percent / aq. NaOH; H2O2 / tetrahydrofuran / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 16.5 percent / NaH / dimethylformamide / 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h 2: 1.) NaBH4, BF3*Et2O, 2.) 30percent H2O2, NaOH / 1.) THF, room temperature, 24 h, 2.) water, 2 h
  • 15
  • [ 6920-24-7 ]
  • 2-tetradecyl-succinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N 2: dimethylformamide
  • 16
  • [ 6920-24-7 ]
  • 2-tetradecylbutane-1,4-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Et3N 2: dimethylformamide 3: H2SO4 4: LiAlH4
  • 17
  • [ 6920-24-7 ]
  • methanesulfonic acid 2-(2-methanesulfonyloxy-ethyl)-hexadecyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Et3N 2: dimethylformamide 3: H2SO4 4: LiAlH4 5: Et3N
  • 18
  • [ 6920-24-7 ]
  • [ 224782-24-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) Bu2SnO; 2.) Et3N / 1.) MeOH, reflux, 2 h; 2.) MeOH, r.t., 10 min 2: 70 percent / TsOH / CH2Cl2 / 2 h / Ambient temperature 3: 76 percent / NaOH / H2O; methanol; CH2Cl2 / 1.5 h / Ambient temperature
  • 19
  • [ 6920-24-7 ]
  • [ 224782-18-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) Bu2SnO; 2.) Et3N / 1.) MeOH, reflux, 2 h; 2.) MeOH, r.t., 10 min 2: 70 percent / TsOH / CH2Cl2 / 2 h / Ambient temperature
  • 20
  • [ 6920-24-7 ]
  • C22H37NO7P(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) Bu2SnO; 2.) Et3N / 1.) MeOH, reflux, 2 h; 2.) MeOH, r.t., 10 min 2: 70 percent / TsOH / CH2Cl2 / 2 h / Ambient temperature 3: 76 percent / NaOH / H2O; methanol; CH2Cl2 / 1.5 h / Ambient temperature 4: 2.) Amberlyte IR-120 (plus) (Na(+)-form) / 1.) CH2Cl2, r.t., 2 h; 2.) MeOH/CH2Cl2, r.t. 5: 51 percent / Amberlist IR-120 (plus) (pyridinium form) / methanol / 2 h / Ambient temperature
  • 21
  • [ 6920-24-7 ]
  • C27H45NO8P(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) Bu2SnO; 2.) Et3N / 1.) MeOH, reflux, 2 h; 2.) MeOH, r.t., 10 min 2: 70 percent / TsOH / CH2Cl2 / 2 h / Ambient temperature 3: 76 percent / NaOH / H2O; methanol; CH2Cl2 / 1.5 h / Ambient temperature 4: 2.) Amberlyte IR-120 (plus) (Na(+)-form) / 1.) CH2Cl2, r.t., 2 h; 2.) MeOH/CH2Cl2, r.t.
  • 22
  • [ 6920-24-7 ]
  • [ 170920-23-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / CCl4 / 0.5 h / Heating 2: NaIO4, RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
  • 23
  • [ 6920-24-7 ]
  • [ 178963-85-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: SOCl2 / CCl4 / 0.5 h / Heating 2: NaIO4, RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 3: 65 percent / NaH / various solvent(s) / 8 h / Ambient temperature 4: 84 percent / H2SO4 / dioxane / 4 h / Ambient temperature
  • 24
  • [ 6920-24-7 ]
  • C22H43O10S(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2 / CCl4 / 0.5 h / Heating 2: NaIO4, RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / Ambient temperature 3: 65 percent / NaH / various solvent(s) / 8 h / Ambient temperature
  • 25
  • [ 6920-24-7 ]
  • [ 97431-37-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 73.8 percent / pyridine / 12 h / 60 °C 2: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h 3: 69.3 percent / acetic acid / tetrahydrofuran; H2O / 4 h / 60 °C 4: 95.4 percent / H2 / Pd-C / ethanol / 20 h / 760 Torr
  • 26
  • [ 6920-24-7 ]
  • [ 80322-78-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 73.8 percent / pyridine / 12 h / 60 °C 2: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h 3: 69.3 percent / acetic acid / tetrahydrofuran; H2O / 4 h / 60 °C 4: 95.4 percent / H2 / Pd-C / ethanol / 20 h / 760 Torr 5: 75.5 percent / pyridine / 0.5 h
  • 27
  • [ 6920-24-7 ]
  • 5-(benzyloxy)-2-tetradecyl-3-oxapentane-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 73.8 percent / pyridine / 12 h / 60 °C 2: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h 3: 69.3 percent / acetic acid / tetrahydrofuran; H2O / 4 h / 60 °C
  • 28
  • [ 6920-24-7 ]
  • 2,2,3,3,11,11,12,12-octamethyl-6-tetradecyl-1,4,7,10,13-pentaoxacyclohexadecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 73.8 percent / pyridine / 12 h / 60 °C 2: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h 3: 69.3 percent / acetic acid / tetrahydrofuran; H2O / 4 h / 60 °C 4: 95.4 percent / H2 / Pd-C / ethanol / 20 h / 760 Torr 5: 75.5 percent / pyridine / 0.5 h 6: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h
  • 29
  • [ 6920-24-7 ]
  • 6-tetradecyl-2,6,13,16,19-pentaoxapentacyclo<18.4.4.47,12.01,20.07,12>dotriacontane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 73.8 percent / pyridine / 12 h / 60 °C 2: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h 3: 69.3 percent / acetic acid / tetrahydrofuran; H2O / 4 h / 60 °C 4: 95.4 percent / H2 / Pd-C / ethanol / 20 h / 760 Torr 5: 75.5 percent / pyridine / 0.5 h 6: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 3 d
  • 30
  • [ 6920-24-7 ]
  • 5-(benzyloxy)-2-tetradecyl-1-(trityloxy)-3-oxapentane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 73.8 percent / pyridine / 12 h / 60 °C 2: 1.) sodium hydride / 1.) THF, 40 deg C, 1 h, 2.) THF, 70 deg C, 20 h
  • 31
  • [ 6920-24-7 ]
  • 2,2,3,3-tetramethyl-9-tetradecyl-1,4,8,11-tetraoxacyclotetradecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 16.5 percent / NaH / dimethylformamide / 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h 2: 1.) NaBH4, BF3*Et2O, 2.) 30percent H2O2, NaOH / 1.) THF, room temperature, 24 h, 2.) water, 2 h 3: 58 percent 4: 4.3 percent / dimethylformamide / 72 h / Heating
  • 32
  • [ 6920-24-7 ]
  • 7-tetradecyl-2,6,9,13-tetraoxatricyclo<12.4.3.01,14>henicosane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 16.5 percent / NaH / dimethylformamide / 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h 2: 1.) NaBH4, BF3*Et2O, 2.) 30percent H2O2, NaOH / 1.) THF, room temperature, 24 h, 2.) water, 2 h 3: 58 percent 4: 2.4 percent / dimethylformamide / 72 h / Heating
  • 33
  • [ 6920-24-7 ]
  • (1R,14S,16R,18R)-1,17,17-trimethyl-7-tetradecyl-2,6,9,13-tetraoxatricyclo<12.4.0.016,18>octadecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 16.5 percent / NaH / dimethylformamide / 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h 2: 1.) NaBH4, BF3*Et2O, 2.) 30percent H2O2, NaOH / 1.) THF, room temperature, 24 h, 2.) water, 2 h 3: 58 percent 4: 3.6 percent / dimethylformamide / 72 h / Heating
  • 34
  • [ 6920-24-7 ]
  • 7-tetradecyl-2,6,9,13-tetraoxatricyclo<12.4.4.01,14>docosane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 16.5 percent / NaH / dimethylformamide / 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h 2: 1.) NaBH4, BF3*Et2O, 2.) 30percent H2O2, NaOH / 1.) THF, room temperature, 24 h, 2.) water, 2 h 3: 58 percent 4: 0.3 percent / dimethylformamide / 72 h / Heating
  • 35
  • [ 6920-24-7 ]
  • [ 156210-20-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 16.5 percent / NaH / dimethylformamide / 1.) 50 deg C, 30 min, 2.) 80 deg C, 24 h 2: 1.) NaBH4, BF3*Et2O, 2.) 30percent H2O2, NaOH / 1.) THF, room temperature, 24 h, 2.) water, 2 h 3: 58 percent
  • 36
  • [ 6920-24-7 ]
  • [ 60742-68-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 63 percent / K / 2-methyl-propan-2-ol / 48 h / Heating 2: 98 percent / oxalyl chloride, pyridine / benzene / 48 h / Ambient temperature
Multi-step reaction with 2 steps 1: (i) K, tBuOH, (ii) /BRN= 605438/
  • 37
  • [ 6920-24-7 ]
  • [ 131618-70-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 63 percent / K / 2-methyl-propan-2-ol / 48 h / Heating 2: 98 percent / oxalyl chloride, pyridine / benzene / 48 h / Ambient temperature 3: 51 percent / triethylamine / benzene / 12 h
  • 38
  • [ 6920-24-7 ]
  • [ 97431-40-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / K / 2-methyl-propan-2-ol / 48 h / Heating 2: 98 percent / oxalyl chloride, pyridine / benzene / 48 h / Ambient temperature 3: 51 percent / triethylamine / benzene / 12 h 4: 60 percent / BH3*THF / tetrahydrofuran / 16 h / Heating
  • 39
  • [ 6920-24-7 ]
  • [ 64066-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 63 percent / K / 2-methyl-propan-2-ol / 48 h / Heating 2: 98 percent / oxalyl chloride, pyridine / benzene / 48 h / Ambient temperature 3: 83 percent / triethylamine / benzene / 12 h 4: 52 percent / BH3*THF / tetrahydrofuran / 24 h / Ambient temperature
  • 40
  • [ 6920-24-7 ]
  • [ 56769-17-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 63 percent / K / 2-methyl-propan-2-ol / 48 h / Heating 2: 98 percent / oxalyl chloride, pyridine / benzene / 48 h / Ambient temperature 3: 83 percent / triethylamine / benzene / 12 h
  • 41
  • [ 6920-24-7 ]
  • [ 60742-67-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (i) K, tBuOH, (ii) /BRN= 605438/ 3: benzene 4: LiAlH4 / tetrahydrofuran
  • 42
  • [ 6920-24-7 ]
  • [ 60742-62-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i) K, tBuOH, (ii) /BRN= 605438/ 2: LiAlH4 / tetrahydrofuran
  • 43
  • [ 6920-24-7 ]
  • 2,6-diphenyl-4-piperidone [ No CAS ]
  • [ 152575-38-7 ]
YieldReaction ConditionsOperation in experiment
38% With sodium hydroxide; p-toluenesulfonic acid monohydrate In water; toluene 3 2,6-Diphenyl-4-piperidone 1,2-Hexadecylene Ketal EXAMPLE 3 2,6-Diphenyl-4-piperidone 1,2-Hexadecylene Ketal A solution of 14.6 g (58.0 mmol) of 2,6-diphenyl-4-piperidone and 12.2 g (64 mmol) of p-toluenesulfonic acid monohydrate in 500 mL of toluene is refluxed and the azeotroping water is collected in a Dean Stark trap. When 1 mL of water is collected, 15.0 g (58.0 mmol) of 1,2-hexadecanediol (Aldrich) is added and the reaction is refluxed until another 1 mL of water is collected. The reaction mixture is cooled to room temperature and made basic with 50% aqueous sodium hydroxide solution. The organic layer is separated and the aqueous phase is extracted with toluene (2*100 mL). The combined organic phases are dried over anhydrous magnesium sulfate and the solvent is removed under reduced pressure. 11.0 g (38% yield) of the title compound is isolated after purification by liquid chromatography (LC) (silica gel, ethyl acetate/hexane) followed by recrystallization from ethanol: mp 63°-70° C. Analysis: Calcd for C33 H49 NO2: C, 80.6; H, 10.0; N, 2.8. Found: C, 80.4; H, 10.3; N, 2.6.
  • 44
  • [ 6920-24-7 ]
  • [ 112-64-1 ]
  • 1,2-bis(tetradecanoyloxy)hexadecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
In pyridine 9 Example 9 Example 9 1,2-Hexadecane dimyristate (also called 1,2-bis(tetradecanoyloxy)hexadecane) is synthesised in this example. To a solution of 2.58 g (0.01 mole) of 1,2-hexadecane-diol in 20 mL pyridine is added 4.94 g (0.02 mole) of myristoyl chloride. The reaction mixture is shaken overnight at ambient temperature, filtered, concentrated and refiltered through silica to afford the title compound.
  • 45
  • [ 6920-24-7 ]
  • [ 20445-33-4 ]
  • C36H48F6O6 [ No CAS ]
  • C36H48F6O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; 1-amino-3-(dimethylamino)propane In dichloromethane for 0.416667h;
  • 46
  • [ 6920-24-7 ]
  • [ 124-63-0 ]
  • C17H36O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With amine In dichloromethane at 0℃; for 24h; 2.2 Synthesis of ligands (Scheme 1) General procedure: To a solution of the respective alcohol (50 mmol) in CH2Cl2 (a-d and g-j) or THF (e-f), an excess of mesyl chloride (1.1 equivalents) in THF was slowly added at 0 °C in the presence of pyridine or triethylamine (1.1 equivalents). The reaction mixture was stirred for 24 h, after which time the complete consumption of the starting material (alcohol) was evidenced by TLC (eluent: dichloromethane). The solvent was then evaporated under reduced pressure and the residue thus obtained was washed twice with water and then with saturated brine solution. The product was purified by column chromatography and/or recrystallization. The alkyl mesylate thus obtained was then slowly added at 70 °C to an ethanol solution containing an excess of 1,2-ethanediamine or 1,3-propanediamine. The reaction mixture was stirred for 24 h, after which time the formation of the desired product was evidenced by TLC (eluent: 8:2 dichloromethane/methanol). The solvent was evaporated and the excess of diamine was removed by extraction with dichloromethane and water. The organic layer was concentrated and the residue was purified by column chromatography and/or recrystallization. Yields: (a) 58%, (b) 52%, (c) 46%, (d) 44%, (e) 60%, (f) 53%, (g) 47%, (h) 56%, (i) 48%, and (j) 35%.
  • 47
  • [ 6920-24-7 ]
  • [ 112-80-1 ]
  • iron(III) acetylacetonate [ No CAS ]
  • iron oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (Z)-9-octadecen-1-amine In diphenylether at 37 - 265℃; Inert atmosphere; Preparation of SPIONS Superparamagnetic iron oxide nanoparticles (SPIONs) were prepared according to the method published by Sun.73 Iron(III) acetylacetonate (353 mg, 1 mmol) was mixed with 1 ,2-hexadecanediol (1292 mg, 5 mmol), oleic acid ( 1224 mg, 4.3 mmol), oleic amine (1214 mg, 4.5 mmol) and diphenylether (10 mL) in a 37°C water bath, and stirred under nitrogen. The vial was heated to 200°C on a heating block, with occasional mixing. The reaction mixture was cooled to room temperature, the nitrogen atmosphere was flushed, and the solution was heated to 265°C, and refluxed for 30 minutes under nitrogen protection. The solution was cooled to room temperature. Isopropanol (20 mL) was added to the reaction system, and the particles were recovered by centrifugation (2500 rpm, 5 min). Hexane (1 mL) was added to dissolve the compound, and the solution was centrifuged at 2500 rpm for 5 minutes. The SPIONs were dried, weighed, and hexane was added to bring the concentration up to 10 mg/mL.
  • 48
  • [ 6920-24-7 ]
  • [ 77-76-9 ]
  • [ 13509-55-2 ]
YieldReaction ConditionsOperation in experiment
97% With graphene In neat (no solvent) at 100℃; for 10h; Sealed tube; For a representative procedure: General procedure: A mixture of diol 1 (1mmol), benzaldehyde dimethyl acetal (1.25mol) and graphene (6mg) were stirred for 10h at 100°C. The resulting mixture was filtered on a nylon membrane, washed with a minimum amount of acetone and the crude was carefully concentrated under vacuum giving the corresponding cyclic acetal in excellent purity (>90%) without further purification.
  • 49
  • [ 6920-24-7 ]
  • [ 31643-49-9 ]
  • C32H38N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% Stage #1: hexadecane-1,2-diol; 4-Nitrophthalonitrile In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 154h; Inert atmosphere;
  • 50
  • [ 102-09-0 ]
  • [ 6920-24-7 ]
  • 4-tetradecyl-1,3-dioxolan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In 2-methyltetrahydrofuran at 30℃; for 2h;
  • 51
  • [ 6920-24-7 ]
  • 1-hydroxy-2-hexadecanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With anhydrous tetramethylammonium chloride; glacial acetic acid In lithium hydroxide monohydrate; acetonitrile Electrochemical reaction; chemoselective reaction; General procedure for the electrochemical alcohol oxidation and characterization data General procedure: In a 5 mL IKA ElectraSyn vial (undivided cell) equipped with a stir bar, Me4Cl (164 mg, 1.5mmol), 3 mL MeCN, 75 μL of water, 86 μl AcOH and the corresponding alcohol (0.6 mmol)were placed. The vial was capped with the cell head equipped with a standard IKA ElectraSyngraphite anode and stainless steel cathode. The solution was stirred until all the electrolyte wasdissolved and then a constant current of 5 mA was applied under a stirring speed of 1000 rpm.After 3 - 5 F/mol of charge had been passed. The reaction mixture was analyzed evaporatedunder reduced pressure, and the residue purified using method A or B. Method A: the residuewas diluted with aqueous NaHCO3 and extracted with DCM. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. Method B: the residue was subjected topurification by silica gel column chromatography using petroleum ether/ethyl acetate as eluent.
37% With cerium(III) bromide; dihydrogen peroxide In 1,4-dioxane; lithium hydroxide monohydrate at 20℃;
With sodium chlorine monoxide; glacial acetic acid In lithium hydroxide monohydrate at 20℃; for 19.5h; Inert atmosphere; Additive B Additive B (ADD B) is 1-hydroxy-2-hexadecanone and is prepared as follows. A 2 L 3-necked flask is charged with acetic acid (500 ml) and Vikinol 16 (a commercially available 16 carbon 1,2-dihydroxy alkane from Arkema) (200 g). The flask is equipped with water cooled condenser and nitrogen inlet. Sodium hypochlorite solution (600 ml of a 15% aqueous solution) is charged via a pressure equalizing dropping funnel and added dropwise to the reaction over 2.5 h at room temperature. After stirring for a further 3 h at room temperature and left to stand for 14 hours, the reaction mixture appears as a slurry. The solid is separated by filtration and collected. The solid filtrate is extracted with dichloromethane (3000 ml) which is washed with water (1000 ml) and sodium bicarbonate solution (2×750 mL) and then dried over magnesium sulfate and filtered. The filtrates were vacuum stripped to isolate the product solid wax product.
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