一种制备(3R,4R)-4,7,7-三甲基-6-氧杂二环[3.2.1]辛烷-3,4-二醇的新方法

doi:10.3969/j.issn.0253-2417.2015.01.002

Abstract

Abstract: (3R,4R)-4,7,7-trimethyl-6-oxabicyclo [3.2.1] octane-3,4-diol was prepared by reaction of α-pinene with 30 % H₂O₂ in presence of dodecyl pyridinium peroxyopolyphosphotungstate catalyst (Cat-PW₄). The effects of different reaction factors on the conversion rate and selectivity were investigated. The optimal conditions are as follows: α-pinene, 12.8 mmol; chloroform as solvent, 5 mL; reaction temperature, 40 ℃; Cat-PW₄ as catalyst, 0.2 g; 30 % H₂O₂, 3.3 mL; reaction time, 3 h. Under these conditions, the conversion rate of α-pinene reached 94.7 %, and the selectivity for the title compound reached 39.8 %. The product existed both in aqueous phase and organic phase and could be isolated from reaction mixtures by extraction and re-crystallization. It was structurally identified by means of IR, UV, ¹H NMR, ¹³C NMR, GC/MS, and HR-ESI-MS. Its yield and purity were 11 % and 98 %, respectively.

Key words: (3R,4R)-4,7,7-trimethyl-6-oxabicyclo[3.2.1] octane-3,4-diol, α-pinene, H₂O₂, dodecyl pyridinium peroxyopolyphosphotungstate

CLC Number:

TQ351

HUANG Dao-zhan, ZHU Shou-ji, LAN Hong-yun, LEI Fu-hou. A Novel Method for Preparation of (3R,4R)-4,7,7-Trimethyl-6-oxabicyclo [3.2.1] octane-3,4-diol[J]. Chemistry and Industry of Forest Products, 2015, 35(1): 9-15.

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A Novel Method for Preparation of (3R,4R)-4,7,7-Trimethyl-6-oxabicyclo [3.2.1] octane-3,4-diol

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