2-Chloroethyl vinyl ether → 4-[2-(Ethenyloxy)ethoxy]benzoic acid
Reaction equation
Cl[CH2:2][CH2:3][O:4][CH:5]=[CH2:6].[OH:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14]CC)=[O:13])=[CH:10][CH:9]=1.[OH-].[K+].O.S([O-])(O)(=O)=O.[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN1CCCC1=O.O>[CH:5]([O:4][CH2:3][CH2:2][O:7][C:8]1[CH:18]=[CH:17][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[CH2:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 120 °C
Procedure
76.97 g (722 mmol) of a chloroethylvinylether, 9.70 g (30.1 mmol) of a tetrabutylammoniumbromide, and 100.00 g (602 mmol) of ethyl 4-hydroxybenzoate, all manufactured by Tokyo Kasei Kogyo Co., Ltd. were mixed with an N-methylpyrrolidone solvent and stirred at a temperature of 120° C. for 3 hours so as to be reacted. The resulting solution was diluted with water and extracted with ethyl acetate so as to remove the solvent thereby obtaining a crude ethyl 4-(2-vinyloxyethoxy)benzoate. A solution of 43.69 g (662 mmol) of potassium hydroxide with 85% purity was added to the ester and reacted at a temperature of 100° C. for 6 hours to be hydrolyzed, followed by dilution and precipitation with a solution of 91.40 g (662 mmol) of sodium hydrogensulfate monohydrate thereby obtaining a crude crystal of 4-(vinyloxyethoxy)benzoic acid. The resulting crude crystal was dissolved in acetonitrile so as to be recrystallized thereby obtaining a needle-like crystal of 4-(vinyloxyethoxy)benzoic acid with an HPLC purity of 99.5 percent or higher. The yield was 104.0 g (83%).
Workup
- customto be reacted
- extractionextracted with ethyl acetate so as
- customto remove the solvent
- customthereby obtaining a crude ethyl 4-(2-vinyloxyethoxy)benzoate
- customreacted at a temperature of 100° C. for 6 hours
Sources & evidence
- ORD record
- ord-acc93871e1b74f3b99cc0c662c17f575
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06894141B2
Reaction notes
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