PENATAAN ULANG CLAISEN 4,6-DIALIL-2-METOKSIFENOL MENGGUNAKAN GELOMBANG MIKRO

WIANTHI SEPTIA WITASARI, Drs. Bambang Purwono, M.Sc., Ph.D

2014 | Tesis | S2 Ilmu Kimia

Telah dilakukan sintesis 4,6-dialil-2-metoksifenol dari eugenol melalui reaksi penataan ulang Claisen dengan metode gelombang mikro. Alil eugenil eter disintesis melalui reaksi antara eugenol dengan alil bromida. Hasil alil eugenil eter selanjutnya dilakukan penataan ulang Claisen dengan gelombang mikro, variasi pelarut yang digunakan meliputi dimetilformamida, etilen glikol dan polietilen glikol. Penentuan waktu reaksi dilakukan pada 5,10,15, 20 dan 50 menit dengan daya microwave 400 dan 560 W. Analisis hasil dilakukan dengan kromatografi gas-spektroskopi massa. Hasil optimasi menunjukkan bahwa iradiasi gelombang mikro dengan pelarut etilen glikol (21,20%) menghasilkan produk yang lebih tinggi dibandingkan dengan dimetilformamida (13,01%) dan polietilen glikol (8,16%). Penggunaan pelarut etilen glikol dengan waktu iradiasi 50 menit dan daya 400 W dapat digunakan untuk sintesis 4,6-dialil-2-metoksifenol melalui reaksi penataan ulang Claisen. Reaksi menggunakan refluks, membutuhkan waktu 7 jam untuk sintesis 4,6-dialil-2-metoksifenol

Synthesis of 4,6-diallyl-2-methoxyphenol through Claisen rearrangement of eugenol using microwave had been conducted. Allyl eugenyl ether was synthesized by eugenol and allyl bromide. Claisen rearrangement of allyl eugenyl ether was heated under microwave irradiation. Variation of solvent was performed using dimethylformamide, ethylene glycol and polyethylene glycol. The time of reaction was performed at 5, 10, 15, 20 and 50 min and the power of microwave at 400 and 560 W. Elucidation of the products has been carried out by using gas chromathography-mass spectroscopy. The result showed that ethylen glycol solvent (21.20%) higher product than dimethylformamide (13.01%) and polyethylene (8.16%) glycol solvent under microwave irradiation. The use of ethylene glycol solvent with 50 minutes reaction time and 400 W power of microwave can be used for the synthesis of 4,6-diallyl-2-methoxy phenol through Claisen rearrangement reaction. Conventional reaction by reflux, takes 7 hours for the synthesis of 4,6-diallyl-2-methoxy phenol.

Kata Kunci : penataan ulang Claisen, gelombang mikro, alil eugenol