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With Candida antarctica lipase B In cyclohexane at 45℃; for 24 h;
General procedure: A (nano)biocatalyst (10–200 mg/l mmol of dicarboxylic acid) wasintroduced into a 10 mL round-bottom flask. Next, decane (20 wt. percent peracid, internal standard), solvent (0–2 mL/L mmol of acid), dicarboxylicacid (1.0 mmol) and alcohol (2.0–32.8 mmol) were successively added.The reaction mixture was then inserted into the thermostatic shaker(250 rpm) at 25–45 °C and the reaction was carried out for 2–24 h.During the reaction, 10 μl of the samples (diluted with acetonitrile)were periodically collected to monitor the reaction progress by GC-FID.After the completion of the reaction, the (nano)biocatalyst was filteredand washed with 20 mL of cyclohexane. The filtrate was concentratedusing a rotary evaporator (7 mbar, 110 °C, 6 h for di-n-butyl esters and5 mbar, 135 °C, 8 h for 2-ethylhexanol esters) to remove cyclohexaneand alcohols. The esters were purified by column chromatographyusing Al2O3 as the stationary phase and CH2Cl2 as the eluent. NMRspectra are available in Supplementary Information (Figs S9-S24).
Reference：
[1] RSC Advances, 2018, vol. 8, # 66, p. 37835 - 37840
[2] Asian Journal of Chemistry, 2014, vol. 26, # 17, p. 5769 - 5772
[3] Applied Catalysis A: General, 2019, p. 41 - 47
[4] Kobunshi Kagaku, 1945, vol. 2, p. 287,296[5] Chem.Abstr., 1950, p. 5144
With toluene-4-sulfonic acid; In water; at 110℃; under 760.051 Torr; for 1h;Heating / reflux;
To a 1000 ml four neck flask fitted with mechanical agitator, thermometer, Dean and Stark apparatus and water condenser, add 237.5g (2.23 mol on pure substance) 80 wt.-% cyanoacetic acid in water, 44Og (3.38 mol) 2-ethylhexanol and 1.2g (6.3 mmol) p-toluenesulfonic acid monohydrate. Afterwards, the mixture is heated to reflux (1 100C) under atmospheric pressure for 1 hour and the water (both initial and formed) is azeotropically distilled out using a Dean and Stark apparatus returning the upper organic layer to the reactor. After 1 hour and at a temperature of 1300C gradually a vacuum of 400 mbar is applied using a water respirator. The azeotropic distillation is maintained for further 6 hours while gradually increasing the vacuum from 400 mbar to 30 mbar in order to maintain a temperature of 1300C until no further water is removed. After releasing the vacuum the reaction mixture is cooled to 900C. After the addition of about 100ml water (pre heated to 900C), the mixture is stirred at 85-900C for 10 minutes before separation of the phases. The upper organic layer is transferred to a 1000 ml four neck flask fitted with mechanical agitator, thermometer, packed column (ID=30mm, H=I 200mm, packing metal raschid rings D=7mm), water condenser and distillate flasks. Excess 2-Ethylhexanol is distilled out at 130- 1400C under a vacuum of 10-30 mbar. When complete increase the vacuum to 1.5 mbar and distilled out 2-ethylhexyl cyanoacetate at 130-1400C. 2-Ethylhexyl cyanoacetate is obtained as a colourless liquid. The reaction yield is 92% (based on cyanoacetic acid).
With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 3h;
R-3 (1 13 mg; 0.48 mmol) was dissolved in dichloromethane (4 ml_). DCC (99 mg; 0.48 mmol) was added to the solution, followed by the addition of DMAP (6 mg; 0.05 mmol) at 0C. The reaction mixture was stirred for 5 min and a solution of 2-Ethyl-1 -hexanol 3 (62.5 mg; 0.48 mmol) in dichloromethane (4 mL) was then added dropwise. The mixture was stirred for 3 h at rt. Dicyclohexylurea was filtered off, and the filtrate was washed with water, brine and dried (Na2S04). After chromatographic separation the product was obtained R-4 (100 mg; 60% yield).
2-Ethylhexyl 4'-phenylbenzophenone-2-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With toluene-4-sulfonic acid; In toluene; for 3h;Reflux;
1001001 30.2 g (0.1 mole) of <strong>[42797-18-2]4-phenylbenzoyl benzoic acid</strong> from Example 8 was mixed with26.0 g (0.2 moles) of ethylhexanol, 50 ml of toluene, and 2.0 g of toluene sulfonic acid. The mixture was heated to reflux and, within 3 hours, 3 ml of water was separated, and the acid value dropped below 5 mg KOHIg. The mixture was allowed to cool down to room temperature, diluted with 50 ml of methylene dichloride, and extracted three times with 100 ml of saturated sodium bicarbonate solution. Then the solvents were removed by rotary evaporator at 80C (50 hPa). Then the excess of ethylhexanol was removed under reduced pressure of 0.1 hPa at a temperature of 120C. A light brown clear liquid remained.Yield: 38.1 g (91% of theory) Characterization:GC-purity: 99%Mass Spectroscopy (m/z): 415 (M(+) +1 285 (100%), 257, 228, 181, 152UV-spectroscopy: 2 max = 287 nm (ethyl acetate)Acid value: <2 mg KOHIgViscosity: 12 Pa.s at 25C
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