Potassium Hydroxide → 2-(4Ethoxyphenyl)-3,3,3-trifluoropropanal
Reaction equation
[OH-].[K+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:19]([F:22])([F:21])[F:20])[O:18][CH:13]2C(OC)=O)=[CH:8][CH:7]=1)[CH3:4]>C(O)C.O>[CH2:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]([CH:12]([C:19]([F:20])([F:21])[F:22])[CH:13]=[O:18])=[CH:10][CH:11]=1)[CH3:4]Participants
Procedure
Into a solution of 11.41 g of potassium hydroxide in 80 ml of ethanol and 20 ml of water, 29.55 g of methyl 3-(4-ethoxyphenyl)-2,3-epoxy-4,4,4-trifluorobutyrate was added with ice-cooling. The reaction solution was stirred at room temperature for 17 hours. Thereafter, the reaction solution was poured into ice water. The resulting solution was washed with diethyl ether and adjusted to pH 3 with 10% HCl and extracted twice with diethyl ether. The ether layers were combined and washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under a reduced pressure and the residue was subjected to distillation under a reduced pressure by heating in an oil bath (130°-140° C.) to obtain 14.66 g of the desired aldehyde (b.p. 100°-105° C./0.3 mmHg).
Workup
- temperaturecooling
- washThe resulting solution was washed with diethyl ether
- extractionextracted twice with diethyl ether
- washwashed with saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was removed under a reduced pressure
- distillationthe residue was subjected to distillation under a reduced pressure
- temperatureby heating in an oil bath (130°-140° C.)
Sources & evidence
- ORD record
- ord-5545ce6b9df248cc915994ddfcd0113c
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04840971
Reaction notes
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