Hydrochloric Acid → 3-Difluoromethoxy-2-(o-tolyl)acrylic acid methyl ester
Reaction equation
[Na].[CH3:2][O:3][C:4](=[O:15])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])=[CH:6][OH:7].C1OCCOCCOCCOCCOC1.Cl[CH:32]([F:34])[F:33].[OH-].[Na+].Cl>CN1CCCC1=O.O>[CH3:2][O:3][C:4](=[O:15])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])=[CH:6][O:7][CH:32]([F:34])[F:33]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 5 °C
Procedure
Preparation of ##STR8## 7.76 g of the sodium salt of 3-hydroxy-2-(o-tolyl)-acrylic acid methyl ester and 0.3 g of 15-crown-5 in 160 ml of N-methyl-2-pyrrolidone (NMP) are cooled to 5° C. with stirring. Chlorodifluoromethane is then passed in while simultaneously adding dropwise a solution of 8.5 g of sodium hydroxide in 9.3 ml of water and the reaction mixture is left to react with vigorous stirring at 5°-8° C. for 2 hours. 82 ml of 2N hydrochloric acid are then added dropwise at 0°-8° C. and the phases are separated. The aqueous phase is extracted exhaustively with ethyl acetate and the combined organic phases are washed with a saturated sodium chloride solution. After drying over sodium sulfate, the residue is filtered and concentrated to dryness by evaporation in vacuo. 3-difluoromethoxy-2-(o-tolyl)acrylic acid methyl ester is obtained in the form of a pale yellow oil.
Workup
- waitthe reaction mixture is left
- customto react
- stirringwith vigorous stirring at 5°-8° C. for 2 hours
- customthe phases are separated
- extractionThe aqueous phase is extracted exhaustively with ethyl acetate
- washthe combined organic phases are washed with a saturated sodium chloride solution
- dry with materialAfter drying over sodium sulfate
- filtrationthe residue is filtered
- concentrationconcentrated to dryness by evaporation in vacuo
Sources & evidence
- ORD record
- ord-99071d58d85a48c1917e9a38df6e2781
- Source dataset
- uspto-grants-1998_01
- Patent number
- US05710314
Reaction notes
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