Process for the preparation of high purity norbornene alkanols and derivatives thereof

摘要

A process for the preparation of a variety of high purity norbornene alkanol monomers and their derivatives is disclosed and claimed. Specifically, a process for the preparation of industrial scale high purity norbornene methanol and its silyl ether derivative is disclosed and claimed. The high purity monomers prepared in accordance with the process of this invention are useful in a variety of applications including but not limited to the preparation of high quality and high purity polynorbornenes having utility in a variety of electronic applications, among various other applications.

主权项

1. A process for the preparation of a compound of formula (I): wherein n is an integer from 1 to 10, inclusive, and where one or more of CH2 is optionally substituted with C1-C10-alkyl or C1-C10-perfluoroalkyl; m is an integer from 0 to 2, inclusive; R1, R2 and R3 are the same or different and independently of each other selected from hydrogen, halogen, methyl, ethyl, linear or branched C3-C12-alkyl, C3-C12-cycloalkyl, C6-C12-bicycloalkyl, C7-C14-tricycloalkyl, C6-C10-aryl, C6-C10-aryl-C1-C3-alkyl, C6-C10-heteroaryl, C6-C10-heteroaryl-C1-C3-alkyl, C1-C12-alkoxy, C3-C12-cycloalkoxy, C6-C12-bicycloalkoxy, C7-C14-tricycloalkoxy, C6-C10-aryloxy-C1-C3-alkyl, C6-C10-heteroaryloxy-C1-C3-alkyl, C6-C10-aryloxy, C6-C10-heteroaryloxy and C1-C6-acyloxy; comprising: reacting cyclopentadiene with a compound of formula (II):
CR2R3═CR1—(CH2)n—R  (II) wherein R is —OCOC1-C6-alkyl; at a suitable temperature and conditions, without any solvent, to form a compound of formula (III):and
subjecting compound of formula (III) to suitable trans-esterification agent in the presence of a catalyst to form the compound of formula (I) wherein the compound of formula (I) is prepared in purity higher than 95 percent and essentially free of the corresponding hydrogenated compound of formula (I).