* 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.
With hydroxy-substituted sulfonic acid-functionalized silica (HO-SAS) In tetrahydrofuran at 110℃; Flow reactor
General procedure: Lauric acid (1a) (2.01 g, 10.0 mmol) was dissolved in methanol (10 mL) and then placed in a syringe, which wasthen attached to a syringe pump. The methanol solution was fedinto a stainless steel column (inner volume: 0.53 mL, 4.0 mm i.d. ? 50 mm) filled in HO-SAS (334 mg) with a flow rate of0.177 mL.min-1. The column was immersed into an oil bath(110°C). A back-pressure regulator (75 psi) was connected.The reaction mixture was collected from the outlet. The reaction mixture eluted during the first 10 min was discarded. Thereaction mixture was collected during 3 min and added n-decane as an internal standard for GC analysis. The followingportion was collected for a 30 min period in a glass flask, andsolvent was evaporated. The crude mixture was purified byflash column chromatography on SiO2 (hexane/ethyl acetate =5/1) to give 3a (1.13 g, 99percent).
72 %Chromat.
at 80℃; for 6 h;
General procedure: Equimolar amounts of quaternary ammonium salt (1.5 mmol) and p-toluenesulfonic acid monohydrate (Sigma-Aldrich, 98,5+percent used as received) were mixed in a screw-capped 3 ml vial. The mixture was magnetically stirred and heated to 60 °C until a clear colourless liquid was obtained (about 10 min). DES was used right after its preparation. Equimolar amounts (4.5 mmol) of acid and alcohol were added, and the resulting mixture, was heated to 60 °C (or 80 °C if specified) and magnetically stirred for the specified amount of time. Initially the reaction mixture is homogeneous and fluid, and then a heterogeneous system formed as reaction proceeded, due to insolubility of the esters produced in the DES. For the g.c. analysis further elaboration was as follows. At the end of the reaction, tbutylbenzene was added, as the internal standard, to the mixture, which was then extracted with diethyl ether. Organic layer was washed with NaHCO3, dried over Na2SO4 and analyzed by g.c.
Reference：
[1] Chemistry Letters, 1997, # 1, p. 55 - 56
[2] Chemical and Pharmaceutical Bulletin, 2009, vol. 57, # 7, p. 680 - 684
[3] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 5, p. 607 - 612
[4] Medicinal Chemistry Research, 2011, vol. 20, # 6, p. 769 - 781
[5] Organic Preparations and Procedures International, 2005, vol. 37, # 1, p. 87 - 92
[6] Patent: US6350896, 2002, B1, . Location in patent: Example 6
[7] Agricultural and Biological Chemistry, 1987, vol. 51, # 8, p. 2153 - 2160
[8] Journal of Organic Chemistry, 1959, vol. 24, p. 160,164
[9] Synthetic Communications, 1979, vol. 9, p. 539 - 543
[10] Tetrahedron Letters, 2012, vol. 53, # 38, p. 5151 - 5155
2
[ 112-16-3 ]
[ 67-63-0 ]
[ 10233-13-3 ]
Yield
Reaction Conditions
Operation in experiment
95%
With pyridine In diethyl ether at 0 - 20℃; for 1 h;
General procedure: Based on the GC–MS analysis, three esters were identified in ME. The esters were synthesized toconfirm their activities on adult L. africanus beetles. Dodecanoyl chloride (1.0 g, 4.57 mmol) indiethyl ether (5 ml) was added dropwise to a solution of 3-pentanol (0.41 g, 4.66 mmol) and pyridine(0.37 g, 4.66 mmol) dissolved in diethyl ether (10 ml) at 0°C. The mixture was stirred at room temperature for 60 min. After filtration, the eluate was concentrated and then introducedin an SiO2 column. Elution with 10percent EtOAc in hexane afforded 1.17 g (4.34 mmol, 95percent) of3-pentyl dodecanoate 2 as a colorless oil.
Reference：
[1] PLoS ONE, 2015, vol. 10, # 11,
[2] Journal of the American Oil Chemists' Society, 1947, vol. 24, p. 257
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