* 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 2,6-di-tert-butyl-4-methyl-phenol; potassium carbonate; In acetone; for 2.0h;Heating / reflux;
1.2 g (4.75 mmol) 3-chloro-propionic acid 4-benzoylphenyl ester was dissolved in 12 ml acetone. 10 mg BHT and 1 g (7.13 mmol) anhydric K2CO3 were added. The mixture was refluxed for 2 hours. A TLC analysis (Merck Kieselgel 60F254, eluent ethyl acetate/n.-hexane 30/70) indicated a complete conversion of 3-chloro-propionic acid 4-benzoylphenyl ester to 2-propenoic acid 4-benzoylphenyl ester. The inorganic salts were removed by filtration and the solvent was evaporated under reduced pressure. 0.8 g of 2-propenoic acid 4-benzoylphenyl ester was isolated. Based on TLC analysis, there were no indications for the formation of side products. This analysis was confirmed by 1H-NMR spectroscopy.
With triethylamine; In dichloromethane; water;Flow reactor;
General procedure: For EX-1, the following procedure was carried out using Microreactor B, described above, with the mixing device at ambient temperature. Syringe I contained 15 g BP, 22 g TEA, and 22 g water. Syringe II contained 3 g ACL and 20 g DCM. Each syringe was placed in a separate syringe pump and the pump speeds were controlled to deliver the blends at the flow rates indicated for EX-1 in Table 3 below. The two unused addition ports of the mixing device were sealed with plugs. The molar flow ratios of BP: ACL: TEA pumped to the mixing device were 1: 1.1 :2.9. Separation of aqueous phase and an organic phase was observed in the collection vessel. Analysis of the upper, aqueous phase by NMR indicated approximately 8 mol percent of acrylic acid-TEA salt and approximately 92 mol percent TEA -HQ salt. Analysis of the lower, organic phase by NMR indicated approximately 51 mol percent 4- acryloxybenzophenone (ABP), approximately 0.01 mol percent BP and approximately 42 mol percent of the above mentioned TEA salts. Analysis of the organic layer by GC indicated 95percent Composition of ABP and 2percent of unreacted alcohol. After analysis, the organic layer was washed with water to remove salts and residual TEA. For EX-2 through EX-17, the same procedure was followed but with syringe contents and flow rates as indicated in Table 3. Blend compositions, flow rates, molar flow ratios of BP:ACL:TEA, and percent Composition are provided in Table 3.
With triethylamine; sodium hydroxide; In water; ethyl acetate;
For EX-1, the following procedure was carried out using the microreactor described above, with the mixing device at ambient temperature. Container I contained 100 g BP, 50 g TEA, 20 G NaOH, and 147 g water. Container II contained 40 g ACl and 80 g EtOAc. Each container was connected to a pump and the pump speeds were controlled to deliver the mixtures in the containers at the following rates: Container I; 14 mL/min, or 0.022 mol/min of BP; Container II: 7 mL/min, or 0.028 mol/min of ACl. The two unused addition ports of the mixing device were sealed with plugs. The molar flow ratios of BP:NaOH:TEA:ACl pumped to the mixing device were approximately 1 : 1 : 1 : 1.24. Separation of aqueous phase and an organic phase was observed in the collection vessel. The organic phase was observed to have a hazy appearance. The aqueous layer was removed from the collection vessel. Results of analysis of the organic layer by GC and NMR are presented in Table 1.
Synthesis of 4-acryloyloxy-benzophenone 1.3 g (16.25 mmoli) of NaOH 50percent water solution, were added to a solution of 3 g (15.21 mmol) of 4-hydroxybenzophenone in 20 cc of methyl ethyl ketone. After 30 minutes under stirring, a solution of 1.59 g (15.21 mmol) of methacryloyl chloride in 5 mL of methyl ethyl ketone were added dropwise. After the addition the reaction mixture was stirred for 1 hour, filtered and the solvent was evaporated. The oil residue was purified by flash chromatography on silica gel (eluent CH2Cl2) to obtain 2.74 g of a colourless liquid. 1HNMR (CDCl3): delta (ppm): 2.10 (s, 3H); 5.82 (s, 1H); 6.40 (s, 1H); 7.2-7.3 (m, 2H); 7.45-7.55 (m, 2H); 7.60-7.65 (m, 1H); 7.75-7.85 (m, 2H); 7.85-7.95 (m, 2H)
With triethylamine; In dichloromethane; water;Flow reactor;
General procedure: EX-22 was carried out using Microreactor B. For EX-22, syringe I contained 15 g BP, 33 g TEA, and 33 g water. Syringe II contained 4.2 g 3CPC and 20 g DCM. Each syringe was placed in a separate syringe pump and the pump speeds were controlled to deliver the blends at the flow rates indicated for EX-22 in Table 8 below. The two unused addition ports of the mixing device were sealed with plugs. Separation of aqueous phase and an organic phase was observed in the collection vessel. Analysis of the upper, aqueous phase by NMR indicated approximately 8 mol percent of acrylic acid-TEA salt and approximately 92 mol percent TEA-HC1 salt. Analysis of the lower, organic phase by NMR indicated approximately 51 mol percent ABP, approximately 0.01 mol percent BP and approximately 42 mol percent of the above mentioned TEA salts. Analysis by GC indicated the organic layer was 98percent ABP and 2percent unreacted alcohol. After analysis, the organic layer was washed with water to remove salts and residual TEA. For EX-23 through EX-26, the same procedure was followed as described for EX-22, except that flow rates were as indicated in Table 8. Blend compositions, flow rates, and percent Composition are provided in Table 8.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
