Name: 111-62-6|Ethyl oleate|98%
Brand: Ambeed
SKU: A193804
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1
[ 64-17-5 ]
[ 112-80-1 ]
[ 111-62-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sulfuric acid at 110℃; for 2h;
99.17%	With C₆H₁₅NC₃H₆O₃S3Cl^(1-)H⁽¹⁺⁾Zn⁽²⁺⁾ for 4h; Reflux;	6-8 Example 7 The [N(Et)3C3H6SO3H][ZnCl3] ionic liquid of Example 1 was weighed into 0.05 mol of oleic acid, 0.45 mol of ethanol and 6% of oleic acid, respectively, and added to a three-port system equipped with a reflux condenser, a water separator and magnetic stirring. The flask was heated at reflux temperature for 4 hours. After the reaction was completed, the layer was allowed to stand, and the lower layer of the ionic liquid was separated. The reaction liquid of the upper layer was washed with an alkali solution to remove the remaining reactant, and the obtained crude ester was subjected to rotary distillation to obtain a product oil. Ethyl acetate. The yield of ethyl oleate was 99.17%. The ionic liquid can be reused after being recycled and dried.
97%	With sulfuric acid for 16h; Reflux;	2 Compound 6: To a stirred solution of oleic acid (58 g, 205 mmol) in dry ethanol (580 ml_), cone. H2SO4 (1.094 ml_, 20.53 mmol) was added slowly and the reaction mixture was refluxed for 16h. Upon completion of the reaction as indicated by TLC, the solvent was evaporated under reduced pressure. The residue was cooled to 0 °C, neutralised with satd. aq. NaHCCb solution and extracted with DCM (3 x 250 ml_). The combined organic layers were dried over anhydrous Na2SC>4, filtered and concentrated to obtain ethyl oleate (6, 61.6 g, 198 mmol, 97 % yield) as colorless oil. The ester was taken as such for the next step without further purification. i H (400MHz, CDCh) d 5.39-5.31 (m, 2H), 4.13 (q, 2H, J = 8.0), 2.29 (t, 2H, J = 8.0), 2.02 (app q, 4H, J = 8.0), 1.62 (p, 2H, J = 8.0), 1.35-1.24 (m, 23H), 0.89 (t, 3H, J = 6.0). RT = 3.73 min. 99.5% purity. ESI-MS: m/z = 311 [M+H]+forC2oH39C>2.

97%	With sulfuric acid at 85℃; for 16h; Reflux;	3 [00331] Compound 2: [00332] To a stirred solution of oleic acid (58 g, 205 mmol) in dry EtOH (580 ml_), cone. H2SO4 (1.094 ml_, 20.53 mmol) was added slowly and the reaction mixture was refluxed for 16h. Upon completion of the reaction as indicated by TLC, the solvent was evaporated under reduced pressure. The residue was cooled to 0 °C, neutralised with satd. aq. NaHC03 solution and extracted with DCM (3 x 250 ml_). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated to obtain ethyl oleate (2, 61.6 g, 198 mmol, 97 % yield) as colorless oil. The ester was taken as such for next step without further purification. iH (400MHz, CDCb) d 5.39-5.31 (m, 2H), 4.13 (q, 2H, J = 8.0), 2.29 (t, 2H, J = 8.0), 2.02 (app q, 4H, J = 8.0), 1.62 (p, 2H, J = 8.0), 1.35-1.24 (m, 23H), 0.89 (t, 3H, J = 6.0). RT = 3.73 min. 99.5% purity. ESI-MS: m/z = 311 [M+H]+ for C20H39O2.
95%	With 1-methyl-3-dodecylimidazolium hydrogen sulfate In water at 60℃; for 10h;
93.5%	With mesoporous silica modified Fe₃O₄ nanoparticle fabricated by 3-sulfopropyl-1-(3-propyltrimethoxysilane) imida-zolium hydrogen sulfate at 109.84℃; for 4h; Green chemistry;	2.3 Catalytic activity measurement General procedure: Biodiesel production from oleic acid with alcohol was carried out with FSS-IL as catalyst. In a typical run, oleic acid (10mmol), alcohol (60mmol), and catalyst (0.2g) were added in a flask (50ml) and kept under 373K for 4h. When the reaction was finished, a magnet was put at the bottom of the reaction flask and the catalyst would be totally adsorbed to the magnet. The upper layer was dumped out for analysis and the yield of biodiesel was calculated based on oleic acid referring to previous publication [11]. The left catalyst was washed with acetone for three times, setting in vacuum at 323K for 6h for recycling experiment. The recovered catalyst was also weighted by electronic balance (d=0.0001g) for calculating catalyst mass loss data.
93%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Sealed tube; regioselective reaction;
92%	With SnO₂#dotWO₃ at 80℃; for 2h;
89%	With zirconocene bis(perfluorooctanesulfonate) trihydrate*(tetrahydrofuran) In neat (no solvent) at 80℃; Sealed tube; Green chemistry; chemoselective reaction;
70%	With sulfuric acid at 80℃;
55.5%	Stage #1: cis-Octadecenoic acid With oxalyl dichloride In dichloromethane at 20℃; for 3h; Stage #2: ethanol With pyridine In dichloromethane at 20℃; for 15.5h; Cooling with ice;	Synthesis of Ethyl Oleate Synthesis of Ethyl Oleate [0069] To a chilled solution of oleic acid (5.0 niL, 16 mmol) in methylene chloride (23 mL) was added drop wise oxalyl chloride (2.9 g, 24 mmol) for four minutes. Reaction warmed to room temperature and stirred for 3 hours. Then added drop wise ethanol (9.0 mL) and pyridine (9.0 mL), while cooling the reaction mixture in dry-ice bath. Reaction was stirred at room temperature for 15 hours and diluted with 100 ml methylene chloride and organic phase was washed three times with saturated aqueous solution of sodium bicarbonate (25 mL each), twice with saturated aqueous solution of ammonium chloride (25 mL each) and four times with water (50 mL each). The combined organic phase was dried over MgS04 and filtered using glass frit. After filtration, solvent was removed under reduced pressure and concentrated further using vacuum and heat to obtain yellow oil. The yellow oil was purified by column chromatography using silica gel as the stationary phase and Hexanes:Et20 (5: 1 v/v) as the eluent to yield 2.72 g (55.5%) of ethyl oleate as colorless oil. XH NMR: 0.88 (t, CH3, J = 6.0 Hz), 1.22-1.3 l(m, (CH2)10), 1.25 (m, COOCH2CH3 ), 1.60-1.64 (m, COCH2C), 1.99-2.02 (dt, CH2CH=CHCH2, J = 12 Hz, 6 Hz), 2.28 (t, COC, J = 7.5 Hz), 4.1 1 (q, COOCH2CH3, J = 9.0 Hz), 5.32-5.37 (m, CH=CH). 13C NMR: 14.14 (CH3), 14.31 (COOCH2CH3), 22.73-34.44 (CR2)i3, 60.16 (COOCH2CH3), 129.80-130.04 (CH=CH), 173.88 (COOCH2CH3).
24%	In hexane at 30℃; for 72h; Corynebacterium sp. S-401;
	With hydrogenchloride bei Siedetemperatur;
	With sulfuric acid; toluene bei Siedetemperatur;
	With Twitchell's reagents bei Siedetemperatur;
	With ricinuslipase
	With sulfuric acid
	With toluene-4-sulfonic acid Heating;
	With sulfuric acid at 110℃; for 2h;
	With sulfuric acid at 30℃;
94.6 % Turnov.	at 20℃; for 24h;
95.9 %Chromat.	at 300℃; for 0.233333h;	5.10 An esterification reaction of a fatty acid and alcohol or a transesterification of rapeseed oil and alcohol was conducted using, as a raw material, fats and oils and alcohols shown in Table 7, under conditions of mole ratio, temperature, pressure and reaction time shown in Table 7. Since about 98.5% of rapeseed oil is composed of a tri-glyceride, the reaction from rapeseed oil can be judged to be a transesterification. The reaction product was subjected to HPLC analysis in the same manner as in Example 1, from the HPLC analysis result, conversion into a fatty acid alkyl ester from a fatty acid or rapeseed oil (=yield of alkyl ester) was obtained. The results are shown in Table 7 together with the reaction conditions. TABLE 7 Alcohol/fats and oils Temperature Pressure Reaction Example (mole ratio) Fats and oils Alcohol (° C.) (Mpa) time (min) Yield (%) Example 42/1C18-3 Methanol 300 20 8 96.2 5-1 Example 42/1C18-2 300 20 8 95.1 5-2 Example 42/1C18-1 300 20 8 95.8 5-3 Example 42/1C18-0 300 20 8 94.7 5-4 Example 42/1C16-0 300 20 8 94.0 5-5 Example 42/1 Rapeseed 300 20 15 98.0 5-6 oil Example 42/1 Rapeseed 350 43 4 98.0 5-7 oil Example 42/1C18-3 Ethanol 300 15 12 94.6 5-8 Example 42/1C18-2 300 15 14 97.4 5-9 Example 42/1C18-1 300 15 14 95.9 5-10 Example 42/1C18-0 300 15 15 91.2 5-11 Example 42/1C16-0 300 15 14 91.7 5-12 Example 42/1 Rapeseed 300 15 45 96.7 5-13 oil Example 42/1 Rapeseed 350 25 10 97.1 5-14 oil Example 42/1C18-3 1-propanol 300 10 15 97.0 5-15 Example 42/1C18-2 300 10 14 92.7 5-16 Example 42/1C18-1 300 10 14 92.3 5-17 Example 42/1C18-0 300 10 14 89.6 5-18 Example 42/1C16-0 300 10 14 90.1 5-19 Example 42/1 Rapeseed 300 10 45 96.1 5-20 oil Example 42/1 Rapeseed 350 23 14 98.8 5-21 oil Example 42/1C18-3 1-butonal 300 9 15 97.3 5-22 Example 42/1C18-2 300 9 14 92.4 5-23 Example 42/1C18-1 300 9 14 86.1 5-24 Example 42/1C18-0 300 9 14 82.5 5-25 Example 42/1C16-0 300 9 14 81.1 5-26 Example 42/1 Rapeseed 300 9 45 87.1 5-27 oil Example 42/1 Rapeseed 350 23 14 95.3 5-28 oil Example 42/1 Rapeseed 1-octanol 300 6 45 68.7 5-29 oil Example 42/1 Rapeseed 350 19 20 90.7 5-30 oil C16-0: palmitic acid, C18-0: stearic acid, C18-1: oleic acid, C18-2: linoleic acid, C18-3: linolenic acid
	at 80℃;
	With molecular sieve at 25℃; for 96h;
94 %Chromat.	With phosphotungstic acid at 25℃; for 4h;
	With sulfated titania at 80℃; for 1h;
100 %Chromat.	With mesoporous SiO₂-TiO₂-SO₃H (1SP-4T) at 80℃; for 6h;
	With Candida antarctica lipase B In 2,2,4-trimethylpentane at 60℃;
	With O₄₀PW₁₂^(3-)2.5H⁽¹⁺⁾0.5Cs⁽¹⁺⁾*2H₃N
	With immobilized Bacillus sp. DVL₂ lipase on glutaraldehyde-activated aluminum oxide pellets In hexane at 37℃; for 16h; Enzymatic reaction;	a Application of the immobilized lipase in esterification of ethanol with oleic acid Partially purified lipase immobilized on aluminum oxide pellets was used as biocatalyst for the esteriﬁcation of oleic acid and ethanol in 1:1 (v/v) ratio in hexane. The reaction was carried out at 37 °C with shaking at 100 rpm for 4, 8, 12, 16, 20 and 24 h with heat inactivated free enzyme as control. The ester content was quantified by using the alkalimetric method of titrating unreacted acid with 0.1 N NaOH using phenolphthalein as an indicator. The percentage conversion in ester synthesis was based on the amount of acid consumed [34]. Reusability of the immobilized lipase in the above esterification reaction was also tested.
	With 3-(N,N-dimethyldodecylammonium)propanesulfonic acid p-toluenesulfonate at 60℃; for 3h;
	With lipase from Candida sp. 99-125 In neat (no solvent) at 20℃; for 24h; Molecular sieve; Enzymatic reaction;	2.2.1 General procedures of esterification General procedure: All the esterification experiments were carried out in a 50 mL round bottom flask. The reaction procedure was described as follows: To a mixture of 0.05 mol oleic acid and corresponding alcohol, catalyst was added at the given temperature. Normally, the reactants mixture kept stirring for 24 h until the reaction completed. The samples were taken out every 1 h in the first 12 h, and the acid value was determined according to the standard GB1668-81. In the end, the chromaticity of the oleates was recorded on PFX-i Series from Tintometer Ltd.
	With phosphonic acid polysilsesquioxanes at 90℃; for 10h; Reflux;	Esterification of oleic acid Oleic acid (1 g, 3.54 mmol), catalyst (20 mg, 1.9 mol%) and ethanol (6 mL) were combined and the reaction mixture was refluxed for 8 h then heated to 90 C for 2 h using an air condenser.The evaporated solvent was replaced with dry ethanol and the mixture heated a further 2 h using an air condenser. Ether (30 mL)was added to the cooled mixture and the catalyst was filtered off,washed with diethyl ether and retained for recycling. The organic solvents were removed from the filtrate. Conversion to the ethyloleate was determined by integration of the total alkene proton signal at H 5.33 (m, 2H) against the ester methylene signal at H4.11 (q, 2H, OCH2CH3).
	With sulfated zirconia nanoparticles dispersed in poly(N-vinylpyrrolidone) at 95℃; for 6h;
96.5 %Chromat.	In water at 32℃; for 24h; Enzymatic reaction;
	With toluene-4-sulfonic acid In toluene for 12h; Inert atmosphere; Reflux; Dean-Stark;	2.1.1 Ethyl oleate (2) [21] or (Z)-ethyl-9-octadecenoate Oleic acid (5g, 18mmol) and para-toluene sulfonic acid (42mg, 0.22mmol) were suspended in EtOH-toluene (1:5; 50mL) under an argon atmosphere. The reaction mixture was stirred under reflux for 12h, using a Dean Stark apparatus. (0009) After removal of the solvent under reduced pressure, the residue was dissolved in diethyl ether (50mL) and washed with saturated NaHCO3 (3×50mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give 5.31g (96%) of 2 as a colorless liquid. The crude product was no further purified.
	With tin(II) bromide monohydrate at 59.84℃; for 0.0833333h;
	With chlorosulfonic acid bei Siedetemperatur;
	With 1-hexyl-3-methylimidazolium hydrogen sulphate at 99.84℃; for 6h; Ionic liquid; Inert atmosphere; Green chemistry;
	With [SO₃H-(CH₂)₃-HIM]₃PW₁₂O₄₀ encapsulated iron containing metal organic frame work MIL-100 at 111℃; for 5h;
	With immobilized Candida antarctica lipase B (Cal B) Green chemistry; Enzymatic reaction;
	With zirconium containing 2-aminoterephthalate metal organic framework at 78℃;	Esterification of other saturated (C16, C18) and unsaturated(C18:1, C18:2, C18:3) fatty acids General procedure: In view of the good catalytic activity and recyclability of UiO-type MOFs for the esterification of lauric acid with MeOH and EtOH,we wanted to investigate the applicability of the MOFs to otherbiomass derived free fatty acids with longer chain lengths, bothsaturated and unsaturated. Thus, we extended our study to theesterification with MeOH and EtOH of palmitic (hexadecanoic acid,C16), Stearic (octadecanoic acid, C18), Oleic (cis-9-octadecenoicacid C18:1), linoleic (cis,cis-9,12-octadecadienoic acid, C18:2) and-linolenic acids (cis,cis,cis-9,12,15-octadecatrienoic acid, C18:3).For the sake of brevity, the complete catalytic data obtained for eachfatty acid and the comparison with other acid catalysts from theliterature is provided as Supporting Information (Tables S1-S10).In order to illustrate the dependence of the chain length andunsaturation degree of the fatty acid on reaction rate, Fig. 3 showsthe calculated pseudo-first order reaction rate constants, k, of ester-ification of various fatty acids with ethanol over UiO-66-NH2. Thesame tendency was also observed for UiO-66, although this mate-rial was in general less active than UiO-66-NH2(as already observed C12 for C12 esterification commented above). As it can be observed, thereaction rate decreases as the chain length and the degree of unsa-turation of the fatty acid increases. This is probably due to higheradsorption of the unsaturated fatty acid (or fatty ester) on the sur-face of the solid, which causes the progressive deactivativation ofthe catalyst. However, it is worth mentioning that this deactivationdue to product adsorption is fully reversible, and the activity of thecatalysts is completely recovered by simply washing with EtOH.In conclusion, the above experiments demonstrates that bothZr-containing UiOs can efficiently catalyze the esterification of var-ious fatty acids with MeOH and EtOH, being less active as the alkylchain length and degree of unsaturation of the acid increases. It isalso worth mentioning that in all the reactions tested, the Zr-MOFswere found to be stable and reusable without significant loss ofactivity, as we have previously demonstrated for the esterificationof C12 with EtOH over UiO-66-NH2.
	With calcium ferrite at 70℃; for 4h;
	With candida antarctica lipase B immobilized on accurel MP₁₀₀₀ In n-heptane at 60℃; for 1h; Enzymatic reaction;
	With Candida antarctica lipase B immobilized on magnetite/chitosan nanoparticles In water at 24℃; for 3h;	5 2.2.5 Solvent-free ethyl oleate synthesis Briefly, 1 g of oleic acid (OA), 200 mg distilled water and 150 μL ethanol were magnetically stirred along with 30 mg of CAT at 24 °C for 3 h [8].
	With Novozym 435 In cyclohexane at 57℃; for 2.75h; Enzymatic reaction;	2.3. Reaction settings The reactions started with 0.206 mol L-1of oleic acid,0.712 mol L-1of ethanol, and the corresponding amount of cyclo-hexane as solvent. The temperature was set to 57C, and after it wasstabilized, the catalyst was added. The concentration of the catalystwas 10% w/w in relation to oleic acid. The reactions were mon-itored by using the ATR/FT-IR probe for 165 min. As the reactionprogressed, the PLS model was used for real-time quantification ofeach component. Reactions were performed in triplicate in orderto estimate the experimental variance.
	With candida antarctica B (CALB) lipase immobilized in polyurethane (PU) foam at 40℃; for 0.666667h; Enzymatic reaction;	ethyl oleate he evaluation of the ability of immobilized CALB to catalyze theethyl oleate synthesis was performed using oleic acid and ethanolas substrates, at different molar ratios (1:1, 1:3 and 3:1) (5 g of sub-strates), immobilized CALB 0.1 g, temperature of 40C, 160 rpm for40 min, conditions described before (item 2.8). Then, 500 L wereremoved (in triplicate) from the reaction medium and placed in15 mL of acetone-ethanol solution (1:1) (v/v).
	With C₃₄H₇₄N₂O₆S₂⁽²⁺⁾*2C₇H₇O₃S^(1-) at 60℃; for 4.5h; Ionic liquid; Green chemistry;
	With milling petioles of Carica papaya In 2,2,4-trimethylpentane at 50℃; for 48h; Molecular sieve; Enzymatic reaction;
	With glutaraldehyde functionalized cellulose immobilized candida antarctica lipase B In n-heptane at 60℃; for 1h; Enzymatic reaction;
	With p-sulfonic acid calix[4]arene-functionalized alkyl bridged organosilica at 80℃; for 4h;
	at 100℃; for 6h;	Catalytic tests General procedure: Esterification reactions of carboxylic acids besides oleic acid with alcohols were carried out in a 100 mL round-bottomed flask equipped with a reflux condenser at atmospheric pressure. In a typical run, 0.1 mol (6.0 g) acetic acid, 0.3 mol (13.8 g) ethanol and 0.1 g catalyst were added into the round bottom flask. After stirring for a certain reaction time at the reflux temperature, the catalyst was filtered and the product was determined using a gas chromatograph with flame ionization detector (FID). Esterification reactions of oleic acid with alcohols were carried out in a 50 mL gas-tight batch reactor with a magnetic stirrer, and an oil bath was used to maintain the reaction temperature. In a typical run,0.07 g PI-HPM (5 wt.% (0.5 mol%) of oleic acid) were added to the mixture of oleic acid (5 mmol, 1.41 g) with methanol (50 mmol, 1.6 g), after stirring for 6 h at desired temperature (40, 60, 80 or 100 °C). The products were identified by comparison with the authentic samplesand finally by gas chromatography-mass spectrometry(GC-MS). The conversion of oleic acid was determined using an Agilent 6890 gas chromatograph equipped witha HP-5MS capillary column and FID detector; methyl caprylate was selected as internal standard. Stability test of the PI-HPM was carried out by runningfour consecutive experiments under the same reactionconditions (mole ratio of methanol to oleic acid: 10:1,reaction temperature: 80 °C, catalyst amount: 10 wt.% ofthe weight of oleic acid and reaction time: 6 h). Betweenthe catalytic experiments, the catalyst was separated fromthe reaction mixture by filtration, washed with methanoland dried at 110 °C.
	With Cu₃(BTC)₂ modified with [HVIm-(CH₂)₃SO₃H]HSO₄ at 90℃; for 4h;
	With POSS-[VMPS][H₂SO₄] at 70℃; for 3h;	2.2 Procedure for catalytic performance General procedure: The esterification reactions were performed using oleic acid with different alcohols (methanol, ethanol, propanol and butanol) at different temperatures. Taking the esterification of oleic acid with methanol as an example, 0.01mol oleic acid, 0.2mol methanol, and 0.2mmol catalyst were added into a 50mL round-bottomed flask equipped with a reflux condenser. The mixture was reacted at 70°C for 3h without the addition of any solvents. Notably, the reactions performed at high temperatures (100°C and 120°C) were carried out in a 50mL autoclave. After the reaction, the solid catalyst can be easily recovered by centrifugation, and the reaction product was determined by GC-MS.
	With asparaginium nitrate In chloroform at 70℃; for 5h; Green chemistry;
	at 160℃; for 18h; Autoclave; Green chemistry;
	With sulfobutylether-β-cyclodextrin at 60℃; for 1.5h;	General procedure for the synthesis of biodiesel. General procedure: To a fl ask was added different volume of SB-CDsolution, the solvent was evaporated by evaporatorand dried under vacuum at 40°C for 24 h, methanol andFFAs were added into the fl ask. The esterifi cation wasthen typically carried out for a length of time at a specifi ctemperature with vigorous stirring. After the reaction, theunreacted alcohol was recovered by distillation. Afterthe residue was cooled and kept for a while, the reactionmixture became biphasic. The upper phase containing thedesired biodiesel could be collected by decantation; thebottom phase, a mixture of catalyst and water generatedfrom the reaction, could be reused after removal of water(Fig. 1). Conversion data were calculated based on FFAsthrough KOH titration [24].
	With sulfuric acid at 40℃; for 12h; diastereoselective reaction;
	With Candida antarctica lipase B immobilized on covalent organic framework In n-heptane at 70℃; for 1h;
	With Thermomyces lanuginosus lipase at 37℃; for 24h; Enzymatic reaction;

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[31]He, Leqin; Qin, Shenjun; Chang, Tao; Sun, Yuzhuang; Gao, Xiaorui [Catalysis science and technology, 2013, vol. 3, # 4, p. 1102 - 1107]
[32]Zhong, Hui; Fang, Zheng; Zou, Baohua; Li, Xin; Ouyang, Pingkai; Guo, Kai [Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 90, p. 114 - 117]
[33]Sebah, Majda; Maddala, Sai P.; Haycock, Peter; Sullivan, Alice; Toms, Harold; Wilson, John [Journal of Molecular Catalysis A: Chemical, 2013, vol. 374-375, p. 59 - 65]
[34]Chen, Guochang; Guo, Cun-Yue; Qiao, Hongbin; Ye, Mingfu; Qiu, Xiaoning; Yue, Caibo [Catalysis Communications, 2013, vol. 41, p. 70 - 74]
[35]Rosset, Isac G.; Cavalheiro, Maria Cecilia H. T.; Assaf, Elisabete M.; Porto, Andre L. M. [Catalysis Letters, 2013, vol. 143, # 9, p. 863 - 872]
[36]Luvino, Delphine; Khiati, Salim; Oumzil, Khalid; Rocchi, Palma; Camplo, Michel; Barthélémy, Philippe [Journal of Controlled Release, 2013, vol. 172, # 3, p. 954 - 961]
[37]Ferreira, Arthur Batista; Cardoso, Abiney Lemos; Da Silva, Marcio Jose [Catalysis Letters, 2013, vol. 143, # 11, p. 1240 - 1246]
[38]Gonzales [Ciencia, 1947, vol. 8, p. 175,176][Chem.Abstr., 1949, p. 127]
[39]Jiang, Dongyu; Chen, Li; Wang, Aili; Yan, Zongcheng [RSC Advances, 2014, vol. 4, # 97, p. 54427 - 54433]
[40]Wan, Hui; Chen, Chong; Wu, Zuowang; Que, Yigen; Feng, Yu; Wang, Wei; Wang, Lei; Guan, Guofeng; Liu, Xiaoqin [ChemCatChem, 2015, vol. 7, # 3, p. 441 - 449]
[41]De Souza, Stefânia P.; Bassut, Jonathan; Marquez, Heiddy V.; Junior, Ivaldo I.; Miranda, Leandro S. M.; Huang, Youkui; Mackenzie, Grahame; Boa, Andrew N.; De Souza, Rodrigo O. M. A. [Catalysis science and technology, 2015, vol. 5, # 6, p. 3130 - 3136]
[42]Cirujano; Corma; Llabrés I Xamena [Catalysis Today, 2015, vol. 257, # Part 2, p. 213 - 220]
[43]Ong, Huei Ruey; Rahman Khan, Md Maksudur; Yousuf, Abu; Hussain, Nor Amalina; Cheng, Chin Kui [RSC Advances, 2015, vol. 5, # 121, p. 100362 - 100368]
[44]Silva, Marcus V. M.; Bassut, Jonathan F.; Junior, Ivaldo I.; De Souza, Stefania P.; Estrada, Melissa L. G.; Miranda, Leandro S. M.; De Souza, Rodrigo O. M. A. [RSC Advances, 2015, vol. 5, # 124, p. 102409 - 102415]
[45]Nicolás, Paula; Lassalle, Verónica L.; Ferreira, María L. [Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 122, p. 296 - 304]
[46]Kartnaller, Vinicius; Junior, Ivaldo I.; De Souza, Adriana V.A.; Costa, Ingrid C.R.; Rezende, Michelle J.C.; Da Silva, João F. Cajaiba; De Souza, Rodrigo O.M.A. [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 123, p. 41 - 46]
[47]Nyari, Nadia Ligianara D.; Fernandes, Ilizandra A.; Bustamante-Vargas, Cindy E.; Steffens, Clarisse; De Oliveira, Débora; Zeni, Jamile; Rigo, Elisandra; Dallago, Rogério M. [Journal of Molecular Catalysis B: Enzymatic, 2016, vol. 124, p. 52 - 61]
[48]Chang, Tao; He, Leqin; Zhang, Xiaojing; Yuan, Mingxia; Qin, Shenjun; Zhao, Jiquan [Chinese Journal of Catalysis, 2015, vol. 36, # 7, p. 982 - 986]
[49]Armendáriz-Ruiz, Mariana; Mateos-Díaz, Eduardo; Rodríguez-González, Jorge Alberto; María Camacho-Ruiz, Rosa; Gutiérrez-Mora, Antonia; Sandoval-Fabian, Georgina; Gallegos-Tintoré, Santiago; Mateos-Díaz, Juan Carlos [Biocatalysis and Biotransformation, 2015, vol. 33, # 4, p. 216 - 223]
[50]De Souza, Stefânia P.; Junior, Ivaldo I.; Silva, Guilherme M. A.; Miranda, Leandro S. M.; Santiago, Marcelo F.; Leung-Yuk Lam, Frank; Dawood, Ayad; Bornscheuer, Uwe T.; De Souza, Rodrigo O. M. A. [RSC Advances, 2016, vol. 6, # 8, p. 6665 - 6671]
[51]De Assis; Abranches; Braga; Zuñiga; Sathicq; Romanelli; Sato; Fernandes [RSC Advances, 2016, vol. 6, # 29, p. 24285 - 24289]
[52]Liu, Lijun; Wang, Honghong; Gong, Shuwen; Lu, Jing; Zhang, Qian [Journal of the Brazilian Chemical Society, 2016, vol. 27, # 6, p. 1007 - 1013]
[53]Chen, Chong; Wu, Zuowang; Que, Yigen; Li, Bingxue; Guo, Qirui; Li, Zhong; Wang, Lei; Wan, Hui; Guan, Guofeng [RSC Advances, 2016, vol. 6, # 59, p. 54119 - 54128]
[54]Lu, Dan; Zhao, Jiwei; Leng, Yan; Jiang, Pingping; Zhang, Chenjun [Catalysis Communications, 2016, vol. 83, p. 27 - 30]
[55]Li, Jingbo; Guo, Zheng [ChemSusChem, 2017, vol. 10, # 8, p. 1792 - 1802]
[56]Dalu, Francesca; Scorciapino, Mariano A.; Cara, Claudio; Luridiana, Alberto; Musinu, Anna; Casu, Mariano; Secci, Francesco; Cannas, Carla [Green Chemistry, 2018, vol. 20, # 2, p. 375 - 381]
[57]Zhang, Guangqing; He, Leqin; Yuan, Mingxia; Li, Hui; Chang, Tao; Qin, Shenjun [Russian Journal of Applied Chemistry, 2018, vol. 91, # 7, p. 1123 - 1128][Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2018, vol. 91, # 7, p. 1123 - 1128,6]
[58]Selva, Elisabet; Soto, J. Javier; Nájera, Carmen; Foubelo, Francisco; Sansano, José M. [Tetrahedron, 2019, vol. 75, # 10, p. 1378 - 1386]
[59]Oliveira, Felipe L.; de Souza, Stefania P.; Bassut, Jonathan; Álvarez, Heiddy M.; Garcia-Basabe, Yunier; Alves de Souza, Rodrigo O. M.; Esteves, Pierre M.; Gonçalves, Raoni S. B. [Chemistry - A European Journal, 2019, vol. 25, # 69, p. 15863 - 15870]
[60]Noro, Jennifer; Cavaco-Paulo, Artur; Silva, Carla [ChemCatChem, 2021, vol. 13, # 21, p. 4524 - 4531]

2
[ 111-62-6 ]
[ 544-35-4 ]
[ 1593-55-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; acetone

Reference： [1]Fujita et al. [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 119][Chem.Abstr., 1955, p. 1565]

3
[ 111-62-6 ]
[ 124-19-6 ]
[ 3433-16-7 ]

Yield	Reaction Conditions	Operation in experiment
	With ozone; acetic acid Behandeln der Reaktionsloesung mit Zinkstaub und Wasser;
	Stage #1: oleic acid ethyl ester With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 6h; Stage #2: With sodium periodate In water; acetone for 2h;

Reference： [1]Helferich; Schaefer [Chemische Berichte, 1924, vol. 57, p. 1914]
[2]Volchkov, Ivan; Park, Sangho; Lee, Daesung [Organic Letters, 2011, vol. 13, # 13, p. 3530 - 3533]

4
[ 111-62-6 ]
[ 112-92-5 ]
[ 143-28-2 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc chromite at 300℃; Hydrogenation;
	With zinc molybdate at 300℃; Hydrogenation;

Reference： [1]Sauer; Adkins [Journal of the American Chemical Society, 1937, vol. 59, p. 2]
[2]Sauer; Adkins [Journal of the American Chemical Society, 1937, vol. 59, p. 2]

5
[ 111-62-6 ]
[ 143-28-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With methanol; Na/SiO<SUB>2</SUB> In tetrahydrofuran at 0 - 25℃; for 0.583333h; Inert atmosphere;
95%	Stage #1: oleic acid ethyl ester With sodium triethylborohydride In diethyl ether; toluene at 20℃; for 8h; Inert atmosphere; Stage #2: With sodium hydroxide In methanol; diethyl ether; toluene at 20℃; for 2h;
92.62%	With lithium aluminium tetrahydride In diethyl ether for 0.5h; Heating;

85%	With ethylmagnesium bromide; poly(methylhydrosiloxane) In tetrahydrofuran; diethyl ether for 1.5h; Ambient temperature;
	With sodium; toluene; butan-1-ol
	With sodium; xylene; <i>tert</i>-butyl alcohol
	With ethanol; sodium
	With lithium aluminium tetrahydride In diethyl ether
	With bis(cyclopentadienyl)titanium dichloride; sodium hydroxide; n-butyllithium; Triethoxysilane 1.) THF, hexane, from -78 deg C to RT, 2.) THF, hexane, 1 h; Yield given. Multistep reaction;
	With C₃₀H₃₄Cl₂N₂P₂Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; for 5h; Glovebox; Autoclave; chemoselective reaction;	28 Example 28: Chemoselective hydrogenation of ester compounds catalyzed by ruthenium complex Ia General procedure: In a glove box, add a ruthenium complex Ia (0.7 mg, 0.001 mmol),Potassium methoxide (35-175 mg, 0.5-2.5 mmol), tetrahydrofuran (5-20 mL), and ester compounds (10-50 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 ° C for 10 to 24 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 6.

Reference： [1]Bodnar, Brian S.; Vogt, Paul F. [Journal of Organic Chemistry, 2009, vol. 74, # 6, p. 2598 - 2600]
[2]Peng, Dongjie; Zhang, Mintao; Huang, Zheng [Chemistry - A European Journal, 2015, vol. 21, # 42, p. 14737 - 14741]
[3]Verba, G. G.; Abdukakharov, V. S.; Abduvakhabov, A. A. [Chemistry of Natural Compounds, 1985, vol. 21, # 5, p. 655 - 657][Khimiya Prirodnykh Soedinenii, 1985, # 5, p. 698 - 700]
[4]Barr, Kenneth J.; Berk, Scott C.; Buchwald, Stephen L. [Journal of Organic Chemistry, 1994, vol. 59, # 15, p. 4323 - 4326]
[5]Oyamada [Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1929, vol. <1>18, p. 633][Chemisches Zentralblatt, 1930, vol. 101, # I, p. 2384]
[6]Hansley [Industrial and Engineering Chemistry, 1947, vol. 39, p. 58]
[7]Bouveault; Blanc [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1903, vol. 137, p. 328][Bulletin de la Societe Chimique de France, 1904, vol. <3>31, p. 1208][Chemisches Zentralblatt, 1905, vol. 76, # II, p. 1700] Toyama [Chemische Umschau auf dem Gebiet der Fette, Oele, Wachse und Harze, 1924, vol. 31, p. 15][Chemisches Zentralblatt, 1924, vol. 95, # I, p. 1216]
[8]Epshtein,A.E. et al. [Pharmaceutical Chemistry Journal, 1977, vol. 11, # 9, p. 1238 - 1242][Khimiko-Farmatsevticheskii Zhurnal, 1977, vol. 11, # 9, p. 81 - 86]
[9]Berk, Scott C.; Kreutzer, Kristina A.; Buchwald, Stephen L. [Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5093 - 5095]
[10]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN110357923, 2019, A Location in patent: Paragraph 0307-0310

6
[ 111-62-6 ]
[ 10335-69-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium ethanolate oleynehydroxamic acid;

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

7
[ 111-62-6 ]
(+/-)-threo-9,10-dihydroxy-octadecanoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With peracetic acid at 30℃;

Reference： [1]Smit [Recueil des Travaux Chimiques des Pays-Bas, 1930, vol. 49, p. 681]

8
[ 111-62-6 ]
[ 79912-54-2 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether; bromine at -10℃; ethyl ester of racemicene oleic acid dibromide;

Reference： [1]Zummo [Archivio di Scienze Biologiche, 1938, vol. 24, p. 165][Chemisches Zentralblatt, 1939, vol. 110, # I, p. 461]

9
[ 111-62-6 ]
[ 103388-72-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; sodium hydride; xylene
	With sodium ethanolate In ethanol for 5h; Inert atmosphere; Reflux;	2.1.2 (9Z, 28Z)-19-[(7Z)-7-hexadecenyl]-9,28-heptatriacontadiene-18,20-dione (3) Ethyl oleate (5g, 16mmol) and freshly prepared sodium ethylate (548mg, 8mmol) were stirred and warmed under reduced pressure until the reaction was completed (no more boiling ethanol). The reaction was next allowed to reach room temperature and acetic acid (30%, 3mL) was added. The residue was dissolved in dichloromethane (100mL) and washed with brine (3×50mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to give 4.55g (49%) of 3 as a yellow oil, which was not further purified.

Reference： [1]Clement [Journal des Recherches du Centre National de la Recherche Scientifique, 1957, vol. 8, p. 160,164]
[2]Luvino, Delphine; Khiati, Salim; Oumzil, Khalid; Rocchi, Palma; Camplo, Michel; Barthélémy, Philippe [Journal of Controlled Release, 2013, vol. 172, # 3, p. 954 - 961]

10
[ 111-62-6 ]
[ 3433-16-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: oleic acid ethyl ester With ozone In dichloromethane at -60℃; for 5h; Stage #2: With triphenylphosphine In dichloromethane at 20℃; for 18h; Inert atmosphere;
89%	With ozone In methanol at -20℃;
	With ethyl acetate bei der Ozonierung bei -40grad und anschliessenden Hydrierung an Palladium;

	(i) O₃, CH₂Cl₂, (ii) Ph₃P; Multistep reaction;
	With ozone Yield given;

Reference： [1]Kudo, Fumitaka; Asou, Yusaku; Watanabe, Moe; Kitayama, Takashi; Eguchi, Tadashi [Synlett, 2012, vol. 23, # 12, p. 1843 - 1846]
[2]Nakajima; Okamura; Takeda; Sugawa; Tateishi; Iwasa; Baba [Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 3, p. 551 - 552]
[3]Stoll; Rouve [Helvetica Chimica Acta, 1944, vol. 27, p. 957]
[4]Bestmann; Stransky; Vostrowsky; Range [Chemische Berichte, 1975, vol. 108, # 11, p. 3582 - 3595]
[5]Masuda, Masahiro; Okawa, Ei-i-chi; Nishimura, Ki-i-chi; Yunome, Hideo [Agricultural and Biological Chemistry, 1984, vol. 48, # 11, p. 2707 - 2710]

11
[ 111-62-6 ]
[ 111-61-5 ]

Yield	Reaction Conditions	Operation in experiment
96%Chromat.	With hydrogen; In ethanol; water; at 23℃; under 760.051 Torr;	General procedure: Volumetric setup for hydrogenation [15] consisted ofthermostated glass reactor with a jacket and a gasburette. 10 mL of 95% ethanol, 50 mg of 5%Pd/C-SiO2 containing 2.5 mg (0.024 mmol) of Pd, 2.34 mmolof ketone or ester were put in a 30 mL reactor. Thereaction was performed with stirring at atmosphericpressure and 23±1. The volume of consumed hydrogenwas measured at constant pressure by matchingthe levels of a liquid in the burette and in theequilibrating vessel. After the hydrogenation wascomplete (the volume of consumed hydrogen becameconstant), 0.20 g (2.34 mmol) of ethyl acetate wasadded to the mixture, and the catalyst was filtered off.The composition and yield of the products weredetermined by GLC. Physico-chemical properties ofthe prepared compounds coincided with the referencedata [16-18].

Reference： [1]Chemische Berichte,1908,vol. 41,p. 1478
[2]Journal of Biological Chemistry,1924,vol. 59,p. 921
[3]Patent: DE187788,
[4]Biochemische Zeitschrift,1909,vol. 22,p. 430
[5]Chemisches Zentralblatt,1918,vol. 89,p. 611
[6]Journal of the American Chemical Society,1962,vol. 84,p. 2829 - 2830
[7]Cuihua Xuebao/Chinese Journal of Catalysis,2011,vol. 32,p. 280 - 285
[8]Transition Metal Chemistry,2012,vol. 37,p. 367 - 372
[9]Russian Journal of General Chemistry,2018,vol. 88,p. 195 - 198
Zh. Obshch. Khim.,2018,vol. 88,p. 215 - 218,4

12
[ 111-62-6 ]
[ 55797-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrachloromethane; mercury(I) chloride; hydrogen fluoride und Erwaermen des Reaktionsprodukts mit wss.Natronlauge;

Reference： [1]Pattison et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 2255,2256][Journal of Organic Chemistry, 1956, vol. 21, p. 883,885]

13
[ 111-62-6 ]
9-fluoro-octadecanoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrachloromethane; mercury(I) chloride; hydrogen fluoride

Reference： [1]Pattison et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 2255,2256][Journal of Organic Chemistry, 1956, vol. 21, p. 883,885]

14
[ 111-62-6 ]
[ 2778-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With copper vanadium oxide at 275℃;

Reference： [1]Sauer; Adkins [Journal of the American Chemical Society, 1937, vol. 59, p. 2]

15
[ 111-62-6 ]
oleic acid oleylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With zinc vanadium oxide at 300℃; Hydrogenation;

Reference： [1]Sauer; Adkins [Journal of the American Chemical Society, 1937, vol. 59, p. 2]

16
[ 111-62-6 ]
(Z)-9,10-epoxyoctadecanoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tris(2,4-pentanedionato)ruthenium(III); Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide In water; acetonitrile at 25℃; for 24h;
76%	With dihydrogen peroxide In isopropyl alcohol at 50℃; for 15h;
	With peracetic acid; acetic acid

Reference： [1]Tenhumberg, Nils; Büttner, Hendrik; Schäffner, Benjamin; Kruse, Daniela; Blumenstein, Michael; Werner, Thomas [Green Chemistry, 2016, vol. 18, # 13, p. 3775 - 3788]
[2]Itoi, Yasushi; Inoue, Masami; Enomoto, Saburo [Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 3941 - 3944]
[3]King [Journal of the Chemical Society, 1949, p. 1817,1823]

17
[ 111-62-6 ]
[ 105-58-8 ]
[ 56472-34-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate unter staendigem Abdestillieren des entstehenden Aethanols und Ansaeuren der Reaktionsloesung mit Essigsaeure;
	With sodium ethanolate unter staendigem Abdestillieren des entstehenden Aethanols und Ansaeuren der Reaktionsloesung mit Essigsaeure;

Reference： [1]Wallingford; Homeyer; Jones [Journal of the American Chemical Society, 1941, vol. 63, p. 2058]
[2]Current Patent Assignee: MALLINCKRODT PUBLIC LIMITED COMPANY - US2367632, 1942, A Current Patent Assignee: MALLINCKRODT PUBLIC LIMITED COMPANY - US2376837, 1942, A Current Patent Assignee: MALLINCKRODT PUBLIC LIMITED COMPANY - US2454360, 1942, A

18
[ 143-18-0 ]
[ 75-03-6 ]
[ 111-62-6 ]

Reference： [1]Journal of Organic Chemistry,1979,vol. 44,p. 2425 - 2429

19
[ 10159-79-2 ]
[ 111-62-6 ]
[ 132370-00-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium In chlorobenzene at 130 - 140℃;

Reference： [1]Tlegenov, R. T.; Dalimov, D. N.; Khaitbaev, Kh. Kh.; Abduvakhabov, A. A.; Uteniyazov, K. U. [Chemistry of Natural Compounds, 1990, vol. 26, # 4, p. 434 - 436][Khimiya Prirodnykh Soedinenii, 1990, # 4, p. 513 - 515]

20
[ 64-17-5 ]
[ 112-62-9 ]
[ 111-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid
	With sodium ethanolate at 25℃; for 1.5h;
	With CpLIP₂ from Candida parapsilosis In aq. phosphate buffer at 30℃; for 0.25h; Enzymatic reaction;

Reference： [1]Krupickova, Jana; Vcelak, Jaroslav; Hetflejs, Jiri [Collection of Czechoslovak Chemical Communications, 1992, vol. 57, # 12, p. 2583 - 2592]
[2]Yao, Linxing; Hammond, Earl; Wang, Tong [Journal of the American Oil Chemists' Society, 2008, vol. 85, # 1, p. 77 - 82]
[3]Subileau, Maeva; Jan, Anne-Hélène; Nozac'h, Hervé; Pérez-Gordo, Marina; Perrier, Véronique; Dubreucq, Eric [Biochimica et Biophysica Acta - Proteins and Proteomics, 2015, vol. 1854, # 10, p. 1400 - 1411]

21
[ 592-47-2 ]
[ 111-62-6 ]
[ 80060-75-9 ]

Yield	Reaction Conditions	Operation in experiment
32%	at 85℃; for 1h;

Reference： [1]Quignard, Francoise; Leconte, Michel; Basset, Jean-Marie [Journal of the Chemical Society. Chemical communications, 1985, # 24, p. 1816 - 1817]

22
[ 111-62-6 ]
[ 19689-19-1 ]
[ 68862-25-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	at 85℃; for 0.5h;

Reference： [1]Quignard, Francoise; Leconte, Michel; Basset, Jean-Marie [Journal of the Chemical Society. Chemical communications, 1985, # 24, p. 1816 - 1817]

23
[ 111-62-6 ]
[ 67-63-0 ]
isopropyl oleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With titanium(IV) isopropylate at 82℃; for 8h;

Reference： [1]Seebach, Dieter; Hungerbuehler, Ernst; Naef, Reto; Schnurrenberger, Peter; Weidmann, Beat; Zueger, Max [Synthesis, 1982, # 2, p. 138 - 141]

24
[ 111-62-6 ]
[ 1779-13-1 ]
[ 80060-80-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 99% 2: 97%	With tetramethylstannane; tungsten(VI) chloride In benzene at 70℃; for 20h;
	With C₄₉H₇₉Cl₂N₂O₃PRuSi In neat (no solvent) at 40℃; for 0.3h; Inert atmosphere; Schlenk technique;

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong [Journal of the American Oil Chemists' Society, 1994, vol. 71, # 8, p. 911 - 913]
[2]Samantaray, Manoja K.; Alauzun, Johan; Gajan, David; Kavitake, Santosh; Mehdi, Ahmad; Veyre, Laurent; Lelli, Moreno; Lesage, Anne; Emsley, Lyndon; Copéret, Christophe; Thieuleux, Chloé [Journal of the American Chemical Society, 2013, vol. 135, # 8, p. 3193 - 3199]

25
[ 111-62-6 ]
[ 80060-75-9 ]
[ 5557-31-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 46% 2: 46%	With tetramethylstannane; tungsten(VI) chloride In benzene at 70℃; for 20h;
1: 46% 2: 46%	With tetramethylstannane; tungsten(VI) chloride In benzene at 70℃; for 20h; other oleates, var. solvents and time;
	With tetramethylstannane; tungsten(VI) chloride In benzene at 70℃; for 20h; Yield given. Yields of byproduct given;

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong; Tan, Daniel D. H. [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 3, p. 333 - 336]
[2]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong; Tan, Daniel D. H. [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 3, p. 333 - 336]
[3]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong; Tan, Daniel D. H. [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 3, p. 333 - 336]

26
[ 111-62-6 ]
[ 56-81-5 ]
[ 122-32-7 ]
1-monooleoyl glycerol [ No CAS ]
1,3-diolein [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 17 mg 2: 5 mg 3: 100 mg	With lipase PS-Celite In acetonitrile at 30℃; for 96h;

Reference： [1]Arcos; Otero [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 6, p. 673 - 682]

27
[ 111-62-6 ]
copper-molybdenum-oxide [ No CAS ]
[ 111-61-5 ]

Reference： [1]Journal of the American Chemical Society,1937,vol. 59,p. 2

28
[ 111-62-6 ]
hydrogen [ No CAS ]
nickel [ No CAS ]
[ 111-61-5 ]

Reference： [1]Chemisches Zentralblatt,1918,vol. 89,p. 611

29
[ 111-62-6 ]
hydrogen [ No CAS ]
palladium black [ No CAS ]
[ 111-61-5 ]

Reference： [1]Biochemische Zeitschrift,1909,vol. 22,p. 430

30
[ 111-62-6 ]
[ 10028-15-6 ]
[ 141-78-6 ]
[ 112-05-0 ]
[ 106-32-1 ]
[ 123-29-5 ]
[ 64-19-7 ]

Reference： [1]Helvetica Chimica Acta,1944,vol. 27,p. 957

Yield	Reaction Conditions	Operation in experiment
	at 250 - 300℃; Hydrogenation;

32
[ 111-62-6 ]
[ 5657-25-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetone
	With pyridine; ethanol

Reference： [1]Jacobson [Journal of the American Chemical Society, 1936, vol. 58, p. 1984] Current Patent Assignee: DUPONT DE NEMOURS INC - US2090594, 1936, A
[2]Stendal [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1933, vol. 196, p. 1810]

33
[ 75-77-4 ]
[ 75-34-3 ]
[ 111-62-6 ]
[(Z)-1-(1,1-Dichloro-ethyl)-1-ethoxy-octadec-9-enyloxy]-trimethyl-silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at -78℃;

Reference： [1]Shiina, Isamu; Imai, Yumiko; Suzuki, Masahiko; Yanagisawa, Manabu; Mukaiyama, Teruaki [Chemistry Letters, 2000, # 9, p. 1062 - 1063]

34
[ 75-34-3 ]
[ 111-62-6 ]
(Z)-2,2-Dichloro-icos-11-en-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at -78℃;

Reference： [1]Shiina, Isamu; Imai, Yumiko; Suzuki, Masahiko; Yanagisawa, Manabu; Mukaiyama, Teruaki [Chemistry Letters, 2000, # 9, p. 1062 - 1063]

35
[ 75-34-3 ]
[ 111-62-6 ]
(Z)-2,2-Dichloro-icos-11-en-3-one [ No CAS ]
(Z)-2,2-Dichloro-3-(1,1-dichloro-ethyl)-icos-11-en-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 21% 2: 23%	With lithium diisopropyl amide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether at -78℃;

Reference： [1]Shiina, Isamu; Imai, Yumiko; Suzuki, Masahiko; Yanagisawa, Manabu; Mukaiyama, Teruaki [Chemistry Letters, 2000, # 9, p. 1062 - 1063]

36
[ 111-62-6 ]
ethyl 9(E)-8,11-dibromooctadecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 4h; Heating;

Reference： [1]Baag, Md. Merajuddin; Kar, Anirban; Argade, Narshinha P. [Tetrahedron, 2003, vol. 59, # 34, p. 6489 - 6492]

37
[ 46118-02-9 ]
[ 111-62-6 ]
3-(3,4-dihydroxyphenyl)propyl oleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With Novozym 435 at 37℃;

Reference： [1]Torres De Pinedo; Peñalver; Rondón; Morales [Tetrahedron, 2005, vol. 61, # 32, p. 7654 - 7660]

38
[ 111-62-6 ]
[ 3897-89-0 ]
4-[(cis-9-octadecenoyloxy)methy]catechol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With Novozym 435 at 37℃;

Reference： [1]Torres De Pinedo; Peñalver; Rondón; Morales [Tetrahedron, 2005, vol. 61, # 32, p. 7654 - 7660]

39
[ 111-62-6 ]
[ 3598-26-3 ]
3,4-dihydroxycinnamyl oleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With Novozym 435 at 37℃;

Reference： [1]Torres De Pinedo; Peñalver; Rondón; Morales [Tetrahedron, 2005, vol. 61, # 32, p. 7654 - 7660]

40
[ 111-62-6 ]
[ 10597-60-1 ]
2-(3,4-dihydroxyphenyl)-ethyl oleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With Novozym 435 at 37℃;
76%	at 60℃; for 24h;	2.A 5 mg of p-toluenesulphonic acid (Aldrich) are added to a solution of 50 mg of hydroxytyrosol (II) in 1.0 mL of ethyl oleate and the resulting mixture is heated at 60 °C for 24 hours. After leaving it to cool, it is washed with a saturated solution of NaHCO3, the organic fraction is gathered, dried over anhydrous sodium sulphate and the mixture is introduced into a chromatography column for purification, with the pure hydroxytyrosol oleate being obtained, with a yield of 76%.Nuclear Magnetic Resonance Spectroscopy (NMR)1H NMR (DMSO-d6) δ : 6.62 (d, 1H), 6.59 (d, 1H), 6.44 (dd, 1H), 5.31 (m, 2H), 4.10 (t, 2H), 2.67 (t, 2H), 223 (t, 2H), 1.97 (q, 4H), 1.47 (m, 2H), 1.25 (m, 20H), 0.84 (t, 3H) ppm.13C (DMSO-d6) δ : 172.7, 145.0, 143.7, 129.6, 128.5, 119.3, 116.1, 115.4, 64.5, 33.7, 33.4, 31.2, 29.0, 28.9, 28.7, 28.6, 28.5, 28.4, 28.3, 26.5, 24.3, 22.0. 13.8 ppmMass Spectrometry (MS) Calculated for C26H43O4 [M+H]+ : 419.316135 Determined by HRMS (Cl) : 419.315427 (1.7 ppm)Element analysis Calculated for C26H42O4 x 1/2 H2O : C, 73.07; H, 10.07 Found : C, 73.58; H, 10.48

Reference： [1]Torres De Pinedo; Peñalver; Rondón; Morales [Tetrahedron, 2005, vol. 61, # 32, p. 7654 - 7660]
[2]Current Patent Assignee: GOVERNMENT OF SPAIN; UNIVERSITY OF SEVILLE - EP1541544, 2005, A1 Location in patent: Page/Page column 7-8

41
[ 112-80-1 ]
[ 78-39-7 ]
[ 111-62-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	In various solvent(s) at 80℃; for 4h;

Reference： [1]Yoshino, Tomonori; Imori, Satomi; Togo, Hideo [Tetrahedron, 2006, vol. 62, # 6, p. 1309 - 1317]

42
[ 67-56-1 ]
[ 111-62-6 ]
[ 112-62-9 ]

Yield	Reaction Conditions	Operation in experiment
	With Dowex 50WX₈-100 at 70℃; for 96h;
	With CpLIP₂ from Candida parapsilosis In aq. phosphate buffer at 30℃; for 0.25h; Enzymatic reaction;

Reference： [1]Oba, Gabriel; Coleman, Bridgett E.; Hart, David J.; Zakin, Jacques; Zhang, Ying; Kawaguchi, Yasuo; Talmon, Yeshayahu [Tetrahedron, 2006, vol. 62, # 43, p. 10193 - 10201]
[2]Subileau, Maeva; Jan, Anne-Hélène; Nozac'h, Hervé; Pérez-Gordo, Marina; Perrier, Véronique; Dubreucq, Eric [Biochimica et Biophysica Acta - Proteins and Proteomics, 2015, vol. 1854, # 10, p. 1400 - 1411]

43
[ 64-17-5 ]
[ 2190-25-2 ]
[ 111-62-6 ]
[ 628-97-7 ]
[ 502-52-3 ]
[ 3123-73-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 45 mmol 2: 11 mmol	With immobilized EL₁ lipase In water; <i>tert</i>-butyl alcohol at 30℃; for 4.16667h;

Reference： [1]Reyes-Duarte, Dolores; Polaina, Julio; Lopez-Cortes, Nieves; Alcalde, Miguel; Plou, Francisco J.; Elborough, Kieran; Ballesteros, Antonio; Timmis, Kenneth N.; Golyshin, Peter N.; Ferrer, Manuel [Angewandte Chemie - International Edition, 2005, vol. 44, # 46, p. 7553 - 7557]

44
[ 122-32-7 ]
[ 64-17-5 ]
[ 111-62-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With zirconocene bis(perfluorooctanesulfonate) trihydrate*(tetrahydrofuran) In neat (no solvent) at 80℃; for 24h; Sealed tube; Green chemistry; chemoselective reaction;
80%	With immobilized lipase from Rhizomucor miehei at 40℃; for 24h;
	With sulfuric acid at 30℃;

0%	at 80℃; for 12h;
	With 1-hexadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide at 60℃; Enzymatic reaction;

Reference： [1]Tang, Zhi; Jiang, Qiutao; Peng, Lifen; Xu, Xinhua; Li, Jie; Qiu, Renhua; Au, Chak-Tong [Green Chemistry, 2017, vol. 19, # 22, p. 5396 - 5402]
[2]Bertram, Mark; Hildebrandt, Petra; Weiner, David P.; Patel, Jesal S.; Bartnek, Flash; Hitchman, Timothy S.; Bornscheuer, Uwe T. [Journal of the American Oil Chemists' Society, 2008, vol. 85, # 1, p. 47 - 53]
[3]Isbell, Terry A.; Green, Lindsay A.; DeKeyser, Stephanie S.; Manthey, Linda K.; Kenar, James A.; Cermak, Steven C. [Journal of the American Oil Chemists' Society, 2006, vol. 83, # 5, p. 429 - 434]
[4]Current Patent Assignee: NATIONAL UNIVERSITY CORPORATION TOKYO INSTITUTE OF TECHNOLOGY - WO2007/913, 2007, A1 Location in patent: Page/Page column 10-11
[5]Location in patent: experimental part De Diego, Teresa; Manjon, Arturo; Lozano, Pedro; Vaultier, Michel; Iborra, Jose L. [Green Chemistry, 2011, vol. 13, # 2, p. 444 - 451]

45
[ 111-62-6 ]
[ 57267-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 89 percent / O₃ / methanol / -20 °C 2: NaBH₄ / ethanol 3: pyridine / 0 °C 4: 6.2 g / LiI / acetone / 14 h / Heating

Reference： [1]Nakajima; Okamura; Takeda; Sugawa; Tateishi; Iwasa; Baba [Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 3, p. 551 - 552]

46
[ 111-62-6 ]
[ 3639-34-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 89 percent / O₃ / methanol / -20 °C 2: NaBH₄ / ethanol

Reference： [1]Nakajima; Okamura; Takeda; Sugawa; Tateishi; Iwasa; Baba [Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 3, p. 551 - 552]

47
[ 111-62-6 ]
[ 189025-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 89 percent / O₃ / methanol / -20 °C 2: NaBH₄ / ethanol 3: pyridine / 0 °C

Reference： [1]Nakajima; Okamura; Takeda; Sugawa; Tateishi; Iwasa; Baba [Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 3, p. 551 - 552]

48
[ 111-62-6 ]
10,11-dioctyleicosane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: WCl₆, SnMe₄ / benzene / 20 h / 70 °C 2: 1.) BF₃ (gas), 2.) H₂ / 2.) 10percent Pd/C / 1.) C₂H₅OH, 30 psi, 90 deg C, 1 h, 2.) 300 psi, 165 deg C, 1 h

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong; Tan, Daniel D. H. [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 3, p. 333 - 336]

49
[ 111-62-6 ]
10,11-dioctyl-10-eicosene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: WCl₆, SnMe₄ / benzene / 20 h / 70 °C 2: BF₃ (gas) / ethanol / 1 h / 90 °C / 1551.4 Torr

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong; Tan, Daniel D. H. [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 3, p. 333 - 336]

50
[ 111-62-6 ]
(E)-10,11-Dioctyl-icos-9-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: WCl₆, SnMe₄ / benzene / 20 h / 70 °C 2: BF₃ (gas) / ethanol / 1 h / 90 °C / 1551.4 Torr

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong; Tan, Daniel D. H. [Journal of the American Oil Chemists' Society, 1996, vol. 73, # 3, p. 333 - 336]

51
[ 111-62-6 ]
[ 542-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 99 percent / WCl₆, SnMe₄ / benzene / 20 h / 70 °C 2: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 3: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong [Journal of the American Oil Chemists' Society, 1994, vol. 71, # 8, p. 911 - 913]

52
[ 111-62-6 ]
[ 157622-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 99 percent / WCl₆, SnMe₄ / benzene / 20 h / 70 °C 2: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C

Reference： [1]Choo, Yuen-May; Ooi, Kay-Eng; Ooi, Ing-Hong [Journal of the American Oil Chemists' Society, 1994, vol. 71, # 8, p. 911 - 913]

53
[ 111-62-6 ]
oleyl iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 92.62 percent / LIAlH₄ / diethyl ether / 0.5 h / Heating 2: 82.5 percent / triethylamine / diethyl ether / 12.5 h / -5 - 0 °C 3: 83.5 percent / NaI / acetone / 3 h / Heating
	Multi-step reaction with 2 steps 1: sodium; butyl alcohol; toluene 2: phosphorus; iodine / 100 - 110 °C

Reference： [1]Verba, G. G.; Abdukakharov, V. S.; Abduvakhabov, A. A. [Chemistry of Natural Compounds, 1985, vol. 21, # 5, p. 655 - 657][Khimiya Prirodnykh Soedinenii, 1985, # 5, p. 698 - 700]
[2]Oyamada [Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1929, vol. <1>18, p. 633][Chemisches Zentralblatt, 1930, vol. 101, # I, p. 2384]

54
[ 111-62-6 ]
[ 94434-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone 3: 70 °C

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

55
[ 111-62-6 ]
heptadec-8-enyl-carbamic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone 3: 70 °C
	Multi-step reaction with 2 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone / und folgendes Erwaermen des entstandenen, nicht trennbaren Gemisches der ψ-Heptadecenyl-isocyanate mit Alkohol
	Multi-step reaction with 2 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone / und folgendes Erwaermen des entstandenen, nicht trennbaren Gemisches der ψ-Heptadecenyl-isocyanate mit Alkohol

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]
[2]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]
[3]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

56
[ 111-62-6 ]
[ 96773-39-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone 3: alkali carbonate

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

57
[ 111-62-6 ]
N-heptadec-8-enyl-N'-phenyl-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetic acid anhydride; acetone / Erwaermen des entstandenen Gemisches von ψ-Heptadecenyl-isocyanaten mit Anilin
	Multi-step reaction with 2 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetic acid anhydride; acetone / Erwaermen des entstandenen Gemisches von ψ-Heptadecenyl-isocyanaten mit Anilin

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]
[2]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

58
[ 111-62-6 ]
O-acetyl-N-elaidoyl-hydroxylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

59
[ 111-62-6 ]
N,O-diacetyl-N-elaidoyl-hydroxylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium ethylate; hydroxylamine hydrochloride 2: acetone 3: acetone

Reference： [1]Nicolet; Pelc [Journal of the American Chemical Society, 1922, vol. 44, p. 1147]

60
[ 111-62-6 ]
ClSO₃Na [ No CAS ]
[ 373-49-9 ]

Reference： [1]Chemische Berichte,1975,vol. 108,p. 3582 - 3595

61
[ 111-62-6 ]
[ 56219-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (i) O₃, CH₂Cl₂, (ii) Ph₃P 2: (i) K, HMPT, (ii) /BRN= 1769505/

Reference： [1]Bestmann; Stransky; Vostrowsky; Range [Chemische Berichte, 1975, vol. 108, # 11, p. 3582 - 3595]

62
fatty acids from sewage scum; extract of [ No CAS ]
[ 64-17-5 ]
hydroxy fatty acid ethyl esters [ No CAS ]
[ 111-62-6 ]
[ 544-35-4 ]
[ 1191-41-9 ]
[ 628-97-7 ]
[ 14010-23-2 ]
[ 111-61-5 ]

Reference： [1]Patent: WO2004/99115,2004,A1 .Location in patent: Page 11-13

63
[ 111-62-6 ]
[ 56-81-5 ]
1,3-diolein [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With immobilized lipase from Rhizomucor miehei In various solvent(s)

Reference： [1]Bertram, Mark; Hildebrandt, Petra; Weiner, David P.; Patel, Jesal S.; Bartnek, Flash; Hitchman, Timothy S.; Bornscheuer, Uwe T. [Journal of the American Oil Chemists' Society, 2008, vol. 85, # 1, p. 47 - 53]

64
[ 111-62-6 ]
9-octadecene-1,18-diethyl dicarboxylate [ No CAS ]
[ 6114-18-7 ]
[ 5557-31-3 ]

Yield	Reaction Conditions	Operation in experiment
	With C₅₀H₇₃Cl₂N₂O₃PRuSi In toluene at 20℃; Inert atmosphere;

Reference： [1]Karame, Iyad; Boualleg, Malika; Camus, Jean-Michel; Maishal, Tarun K.; Alauzun, Johan; Basset, Jean-Marie; Coperet, Christophe; Corriu, Robert J. P.; Jeanneau, Erwan; Mehdi, Ahmad; Reye, Catherine; Veyre, Laurent; Thieuleux, Chloe [Chemistry - A European Journal, 2009, vol. 15, # 44, p. 11820 - 11823]

65
[ 111-62-6 ]
[ 1310803-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 6 h / 20 °C 1.2: 2 h 2.1: tetrahydrofuran / -78 - 20 °C

Reference： [1]Volchkov, Ivan; Park, Sangho; Lee, Daesung [Organic Letters, 2011, vol. 13, # 13, p. 3530 - 3533]

66
[ 111-62-6 ]
[ 1310803-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 6 h / 20 °C 1.2: 2 h 2.1: tetrahydrofuran / -78 - 20 °C 3.1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane; toluene / 4 h / 20 °C

Reference： [1]Volchkov, Ivan; Park, Sangho; Lee, Daesung [Organic Letters, 2011, vol. 13, # 13, p. 3530 - 3533]

67
[ 111-62-6 ]
[ 1310803-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 6 h / 20 °C 1.2: 2 h 2.1: tetrahydrofuran / -78 - 20 °C 3.1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane; toluene / 4 h / 20 °C 4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 48 h / 85 °C / Inert atmosphere

Reference： [1]Volchkov, Ivan; Park, Sangho; Lee, Daesung [Organic Letters, 2011, vol. 13, # 13, p. 3530 - 3533]

68
[ 111-62-6 ]
C₂₉H₃₈O₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 6 h / 20 °C 1.2: 2 h 2.1: tetrahydrofuran / -78 - 20 °C 3.1: (triphenylphosphine)gold(I) chloride; silver hexafluoroantimonate / dichloromethane; toluene / 4 h / 20 °C 4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 48 h / 85 °C / Inert atmosphere 5.1: rhenium(VII) oxide / diethyl ether / 0.17 h / 25 °C / Inert atmosphere

Reference： [1]Volchkov, Ivan; Park, Sangho; Lee, Daesung [Organic Letters, 2011, vol. 13, # 13, p. 3530 - 3533]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	111-62-6	MDL No. :	MFCD00009579
Formula :	C₂₀H₃₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LVGKNOAMLMIIKO-QXMHVHEDSA-N
M.W :	310.51	Pubchem ID :	5363269
Synonyms :	Ethyl oleate

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

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 111-62-6 ]

Quality Control of [ 111-62-6 ]

Related Doc. of [ 111-62-6 ]

Product Details of [ 111-62-6 ]

Safety of [ 111-62-6 ]

Application In Synthesis of [ 111-62-6 ]

[ 111-62-6 ] Synthesis Path-Upstream 1~1

[ 111-62-6 ] Synthesis Path-Downstream 1~68

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry