Potassium Carbonate → 3-Ethyl-4-[3-(4-trifluoromethoxyphenoxy)propyloxy]-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene
Reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:26])[CH:6]=[C:7]([CH3:25])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:33][C:34]([Cl:38])=[CH:35][CH2:36]Cl>CN(C)C=O>[CH2:1]([C:3]1[CH:4]=[C:5]([O:26][CH2:36][CH:35]=[C:34]([Cl:38])[Cl:33])[CH:6]=[C:7]([CH3:25])[C:8]=1[O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]([F:23])([F:24])[F:22])=[CH:16][CH:15]=1)[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 0.6 g of 3-ethyl-4-[3-(4-trifluoromethoxyphenoxy)propyloxy]-5-methylphenol, 0.22 g of potassium carbonate and 10 ml of N,N-dimethylformamide was added dropwise a solution of 0.31 g of 1,1,3-trichloro-1-propene dissolved in 5 ml of N,N-dimethylformamide, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was poured into ice-water, and extracted twice with 100 ml of diethyl ether. The combined ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.5 g of 3-ethyl-4-[3-(4-trifluoromethoxyphenoxy)propyloxy]-5-methyl-1-(3,3-dichloro-2-propenyloxy)benzene (71% yield), nD23.5 1.5150.
Workup
- stirringAfter stirring at room temperature for 12 hours
- extractionextracted twice with 100 ml of diethyl ether
- washThe combined ether layer was washed with water
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated
- customto obtain a crude product
Sources & evidence
- ORD record
- ord-4b78a0d2a5864e53ad793277a6217287
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05872137
Reaction notes
Loading…