Synthetic Anisaldehyde New Technology And Its Application

Anisaldehyde, as one of the most important chemical material or organic intermediates, was widely applied to medicine, cosmetics, food. The reported procedures for the synthesis of Anisaldehyde require the use of dimethyl sulfate which is hazardous. However dimethyl carbonate (dimethyl carbonate, DMC) was a green chemical materials, with non-toxic, and other non-corrosion characteristics in recent years. In this thesis, Anisaldehyde was synthesized from p-hydroxybenzaldehyde with dimethyl carbonate. Then p-methoxycinnamic acid and 5-ethoxycarbonyl-4-(4-m-ethoxyphenyl)-6-m-ethyl-3-dihydro-pyrimidine-2-ketone were synthesized from anisaldehyde with other raw materials. And effect of a variety of key factors such as temperature, time, solvents were researched. Specific results were as follows:1) Anisaldehyde was synthesized from p-hydroxybenzaldehyde with dimethyl carbonate under phase transfer catalysis(PTC) hexadecyltrimethylammonium bromide. The effect of temperature, time, solvent and catalyst of reaction on yield were researched. The result showed the optimal reaction conditions were p-hydroxybenzaldehyde(lOmmol), dimethyl carbonate(100mmol), hexadecyltrimethylammonium bromide(3mmol), potassium carbonate(7mmol), dimethyl sulfoxide(10mL), reaction temperature 130℃, reaction time 3h, the yield was 88%. The structure of anisaldehyde was identified by means of IR,GC-MS and 1HNMR.2) Anisaldehyde was synthesized from p-hydroxybenzaldehyde with dimethyl carbonate by microwave irradiation under phase transfer catalysis(PTC) tetrabutylammoniu-m bromide, The effect of power, time, solvent and catalyst of reaction on yield were researched. The result showed the appropriate reaction were p-hydroxybenzaldehyde (10mmol), dimethyl carbonate (100mmol), tetrabutylammonium bromide (1mmol), potassium carbonate (7mmol), dimethyl sulfoxide(10ml), the power of reaction (680W), the time of reaction (15min), the yied was 91%. The structure of anisaldehyde was identified by means of IR,GC-MS and 1HNMR.3) p-methoxy cinnamic acid was synthesized from anisaldehyde with malonic acid under catalytic N, N-dimethylformamide (DMF), The result showed the appropriate reaction were anisaldehyde(lmmol), malonic(2mmol), N, N-dimethylformamide(1ml), reaction temperature 110℃, reaction time 2h. Yield was 73%. The structure of p-methoxy cinnamic acid was identified by means of IR,GC-MS and 1NMR.4) 5-ethoxycarbonyl-4-(4-m-ethoxyphenyl)-6-methyl-3-dihydropyrimidine-2-ketone was synthesized from anisaldehyde with ethyl acetoacetate and urea as raw materials in the catalyst sodium bisulfate, The result showed the appropriate reaction were anisaldehyde 25mmol (3.4g), anhydrous ethanol 20ml, acetoacetate 25mmol (3.25g), urea 37.5mmol (2.25g),1.5g sodium bisulfate, reaction temperature 70℃, reaction time 1.5h Yield was 84%. The structure of 5-ethoxycarbonyl-4-(4-m-ethoxyphenyl)-6-methyl-3-dihydropyrimi-dine-2-ketone was identified by means of 1HNMR.