Synthesis method of hydroxyl pinacolone retinoate

Abstract

The invention belongs to the technical field of fine organic synthesis, and particularly relates to a synthesis method of hydroxyl pinacolone retinoate. The method comprises the following steps: (1) adding an organic solvent into retinoic acid, adding an amide catalyst, uniformly stirring, and carrying out ice bath; (2) adding phosphorus trichloride into the material obtained in the step (1) under the protection of nitrogen, and reacting; (3) standing to separate out a lower-layer inorganic solution, adding 1-hydroxy-3, 3-dimethyl butane-2-ketone under an ice bath condition, then adding an acid-binding agent, carrying out heat preservation reaction, carrying out reduced-pressure suction filtration on inorganic salt, and carrying out reduced-pressure concentration on a liquid phase; and (4) adding a recrystallization solvent, cooling and crystallizing to obtain the hydroxypinacolone retinoate. The raw materials and reagents adopted by the invention are common chemical reagents, are low in cost and are easy to obtain; the solvent used in the reaction is toluene, and the next reaction can be carried out without separation and purification; the two-step reaction can be completed in the same kettle, less equipment is used, and the equipment utilization rate is high.

Description

Technical field [0001] The invention belongs to the technical field of fine organic synthesis, and particularly relates to a synthesis method of hydroxy pinacol retinoic acid ester. technical background [0002] Vitamin A, also known as retinol, is a natural fat-soluble vitamin. In a broad sense, vitamin A also includes retinol derivatives such as retinal, retinoic acid, retinol acetate and retinol palmitate, etc., and various structures can be mutually transformed. Vitamin A plays an important role in the growth, development, vision and immunity of vertebrates. In recent years, scientists have found that vitamin A has great efficacy in preventing and treating skin aging and other skin problems. As an effective component for preventing and repairing skin aging, it has attracted much attention, and it is used in various topical medicines for skin diseases, and is often added to cosmetics. Vitamin A is unstable due to its long electron-rich conjugated polyene chain, which is easily...

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Problems solved by technology

In the above-mentioned process, the DCC dehydrating agent used in the condensation reaction generates DCU solid waste after the reaction is completed. The inventors roughly calculated that each ton of product produced produces about 900KG of solid waste, which is close to one ton. The three wastes treatment costs high

DCU and DMAP are not easy to remove, and there will be residues in the product. They need to be washed with acidic aqueous solution, resulting in a large amount of waste water, or removed by passing through the chromatographic column. If the method of passing through the chromatographic column is used, the production efficiency will be low and the cost will be high.

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