SINTESIS B-KETO ESTER SEBAGAI SENYAWA ANTARA UNTUK SINTESIS KURKUMINOID

• Main Author: H.S, Irdoni
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/903
• Institution: Institut Teknologi Bandung

A natural ethyl p-metoxycinnamate, had been used for the synthesis of diethyl p-metoxycinnamoyl malonat and ethyl 2-(p-metoxycinnamoyl)-3-oxo-butanoat. Ethyl p-metoxycinnamate was obtained, from rhyzomes of Kaempferia galanga Linn by percolation with ethanol, as a white crystalline compound m.p. 48,5°C - 49,0°C in 9,4% yield. The raw material ethyl p-metoxycinnamate was hydrolized with ethanolic potassium hydroxide to yield p-metoxicinnamic acid, m.p. 171°C - 172°C, and the acid thus obtained was treated with thionylchloride at 40°C- 50°C to give p-metoxycinnamoylchloride as an intermediate product. Treatment of p-metoxycinnmgylchloride with enolic anion of diethyl malonate yielded a yellow needle crystalline diethyl p-metoxycinnamoyl malonat, m.p. 8315°C - 84,0°C , in 68,4% yield. This malonate derivate was hydrolized with ethanolic potassium hydroxide to yield p-metoxycinnamoyl malonic acid, as pale yellow needle, m.p. 174°C - 176°C, in 86,4% yield. Treatment of p-metoxycinnamoylchloride with magnesium ethyl aceto acetic ester yielded ethyl 2-(p-metox_ycinnamoyl)- 3-oxo-butanoat, as pale yellow needle, m.p. 174,5°C - 175,5°C , in 32% yield. The magnesium ethyl aceto acetic ester which was used for this reaction, was obtained from reaction between magnesium, dry ethanol and ethyl aceto acetic ester in dry eter.