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ChemicalBook CAS DataBase List 4-Fluorobenzaldehyde
459-57-4

4-Fluorobenzaldehyde synthesis

15synthesis methods
4-Fluorobenzaldehyde is produced by a commercially feasible process. The process comprises heating a mixture of fluorobenzene and a strong Lewis acid with dissolved hydrogen halide in an atmosphere of carbon monoxide at about 45 to about 100° C. and at a total pressure of about 150 psig up to the maximum pressure rating of the reactor. Formed is a reaction mass containing a Lewis acid complex of 4-fluorobenzaldehyde and at least a halobis(fluorophenyl)methane by-product. The complex is broken by quenching the reaction mass with a Lewis acid-solvating liquid to liberate 4-fluorobenzaldehyde. By-product halobis(fluorophenyl)methane is converted to di(fluorophenyl)methanol to avoid potential corrosion problems and formation of light-sensitive color bodies in the recovered 4-fluorobenzaldehyde.
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Yield:459-57-4 97%

Reaction Conditions:

with bovine liver acetone powder in aq. phosphate buffer;acetone at 20; pH=7.4; for 0.333333 h;Enzymatic reaction;chemoselective reaction;

Steps:

7 4.5. General deprotection protocol

General procedure: A solution of diacetate 2 (1mmol) and BLAP (10mg) in phosphate buffer (50mM, pH 7.4) was stirred in a vortex (200rpm) at 20°C for for an appropriate time as required to complete the reaction. After complete conversion, as indicated by GC or TLC, the reaction mixture was extracted with ethyl acetate (3×15mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuum to give the corresponding aldehyde 1.

References:

Koszelewski, Dominik;Ostaszewski, Ryszard [Bioorganic Chemistry,2019,vol. 93,art. no. 102825]

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