Dibutyl fumarate synthesis
- Product Name:Dibutyl fumarate
- CAS Number:105-75-9
- Molecular formula:C12H20O4
- Molecular Weight:228.28
108-31-6
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105-75-9
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Yield:105-75-9 98%
Reaction Conditions:
with sulfuric acid;acetonitrile at 80 - 85; for 16 - 18 h;
Steps:
Procedure for amino acid/ anhydrides (Table 2, entry 13-15):
General procedure: To a well stirred mixture of amino acid (80 mmol, or anhydride), alcohol (180 mmol) and acetoniitrile (162 mmol), added sulfuric acid (98%, 94 mmol, 5 mL) at room temperature and temperature maintained between 80-85°C for 16-18 h. The reaction mixture was cooled and added to 20% sodium carbonate solution (100 mL). The reaction mass was extracted in CH2Cl2 (50 mL × 2). The combined organic layer was washed with water (100 mL), dried over sodium sufate, and concentrated under reduced pressure to obtain product (60-99%). Most example gave NMR pure product. Where minor impurities are formed, the product was purified over silica gel using ethyl acetate: petroleum ether (1:9).
References:
Dawar, Pankaj;Raju, M. Bagavan;Ramakrishna, Ramesha Andagar [Synthetic Communications,2014,vol. 44,# 6,p. 836 - 846] Location in patent:supporting information
201230-82-2
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105-76-0
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105-75-9
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