Sodium Bicarbonate → 3-(3-Chlorophenyl)prop-2-enoic acid
Reaction equation
C(O[CH:5](OC(=O)C)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)(=O)C.[C:17]([O-:20])(=[O:19])[CH3:18].[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[Cl:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH:5]=[CH:18][C:17]([OH:20])=[O:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
A three-neck flask was charged with 24.26 g of m-chlorobenzylidene diacetate and 6.15 g of sodium acetate, and the mixture was refluxed in a 200° C. oil bath for 9 hours. The mixture was cooled, and 100 g of ethyl acetate was added. Furthermore, saturated sodium hydrogencarbonate aqueous solution was added, and the mixture was sufficiently stirred, to produce m-chlorocinnamic acid which was extracted into a water phase. The water phase was separated, and hydrochloric acid was added till the pH became 2, to precipitate m-chlorocinnamic acid which was secured by filtration. It was washed by water sufficiently and dried in vacuum at 60° C. for 8 hours, being weighed. The purity of the obtained product was analyzed by high performance liquid chromatography. The m-chlorocinnamic acid yield and m-chlorobenzylidene diacetate conversion were obtained from the following formulae:
Workup
- temperatureThe mixture was cooled
Sources & evidence
- ORD record
- ord-10d646e5a2c348ffaf8feaf431dd49dc
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06278019B1
Reaction notes
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