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Citation: QIAN Hongsheng, DONG Jinfeng, LV Shumin, SHANG Zhicai. Synthesis of Citral and Its Intermediates[J]. Chinese Journal of Applied Chemistry, ;2012, 29(3): 270-274. doi: 10.3724/SP.J.1095.2012.00228 shu

Synthesis of Citral and Its Intermediates

1.
a Faculty of Science, Zhejiang University, Hangzhou 310027, China;
2.
b Technology Center of Zhejiang NHU Co. Ltd, Xinchang 312500, China

Corresponding author: SHANG Zhicai,
Received Date: 19 April 2011
Available Online: 7 June 2011
Fund Project: 浙江省重大科技专项(优先主题)工业项目(2008C11053) (优先主题)工业项目(2008C11053)

Using prenal and prenol as precursors,3-methyl-2-butenal diprenyl acetal was obtained via an acetalization reaction using senecioic acid as catalyst.Then an elimination of 3-methyl-2-butenal diprenyl acetal catalyzed by ammonium dihydrogen phosphate yielded the cis/trans-prenyl-3-methyl-butadienyl ether.Further rearrangement of the elimination product through heating produced to the target citral.The conditions of acetalization reaction and elimination reaction were optimized.It was found that a conversion yield of 63%~64% for prenal could be achieved at 70~75℃ for 8 h with 0.3% senecioic acid as catalyst.After azeotropism treatment,the purity and yield of 3-methyl-2-butenal diprenyl acetal are 97.5% and 96.8%,respectively.Using 0.2%~0.5% ammonium dihydrogen phosphate as catalyst,the elimination reaction was carried out at 100~130℃ and 2.66 kPa.The cis/trans-prenyl-3-methylbutadienyl ether was distilled from the reaction batch and its purity and yield are 95.9% and 97.0%,respectively.The rearrangement reaction temperature was 120~130℃,the purity and yield of citral are 97.5% and 90.2%,respectively.
- prenal,
- prenol,
- citral,
- diprenyl acetal,
- dienyl ether,
- organic synthesis
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