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Citation: LI Jian, HU Ming-Gang, DU Wei-Song, AN Zhong-Wei. New Synthetic Method of 1-(Trans-4-(trans-4-n-pentylcyclohexyl)-cyclohexyl)acetylene[J]. Chinese Journal of Applied Chemistry, ;2008, 25(3): 313-316. shu

New Synthetic Method of 1-(Trans-4-(trans-4-n-pentylcyclohexyl)-cyclohexyl)acetylene

1.
Xi'an Modern Chemistry Research Institute, Xi'an 710065

Corresponding author: LI Jian,
Received Date: 25 May 2007
Available Online: 30 October 2007
Fund Project: 陕西省重大科技专项基金资助(2006kz03-G3) (2006kz03-G3)

(Trans-4-(trans-4-n-pentylcyclohexyl)cyclohexyl)acetylene was synthesized with 1-(trans-4-(trans-4-n-pentylcyclohexyl)cyclohexyl)ethylene as starting material via bromine addition,then two molecules of hydrogen bromide were eliminated.The overall yield was 76.7% with a chromatogram purity of 96%.This method is facile to practise and contains a few steps.The impact of elimination conditions on yield was studied.The reaction was finished within 2 h at 80℃,and a cumulative diene by-product turned to be main product when the reaction time was prolonged to 6 h with a yield of 51.5%.The structures of products were identified by IR,MS and NMR.The mechanism of the rearrangement was proposed,i.e.,the hydrogen migrated under the action of alkaline,which resulted in a thermodynamically stable cumulative diene by-product.A new path was provided to obtain cyclohexyl-substituted acetylene or cumulative diene selectively by controlling the reaction conditions.
- cyclohexylacetylene,
- cumulative diene,
- liquid crystal intermediate,
- synthesis,
- elimination
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