Dichloroacetyl chloride → 1-(4-Chlorophenoxy)-1-(imidazol-1-yl)-2-dichloroacetoxy-3,3-dimethyl-4-chloro-butane
Reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][CH:7]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[CH:8]([OH:14])[C:9]([CH3:13])([CH3:12])[CH2:10][Cl:11])=[CH:4][CH:3]=1.[Cl:22][CH:23]([Cl:27])[C:24](Cl)=[O:25]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[CH:8]([O:14][C:24](=[O:25])[CH:23]([Cl:27])[Cl:22])[C:9]([CH3:12])([CH3:13])[CH2:10][Cl:11])=[CH:20][CH:21]=1Participants
Procedure
19.8 g (0.06 mol) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chlorobutan-2-ol were added to 200 ml of dichloroacetyl chloride at 0° C. The mixture was stirred at room temperature for 24 hours and excess dichloroacetyl chloride was distilled off in vacuo. The oil which remained was taken up in 400 ml of methylene chloride, the methylene chloride mixture was neutralized with 500 ml of aqueous sodium bicarbonate solution, the organic phase was separated off, washed with 200 ml of water and dried over sodium sulphate. The solvent was distilled off and the residue was taken up in 200 ml of diisopropyl ether. After leaving the mixture to stand for several hours, colorless crystals precipitated. 7.5 g (29% of theory) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-2-dichloroacetoxy-3,3-dimethyl-4-chloro-butane of melting point 108°-110° C. were obtained.
Workup
- distillationexcess dichloroacetyl chloride was distilled off in vacuo
- customthe organic phase was separated off
- washwashed with 200 ml of water
- dry with materialdried over sodium sulphate
- distillationThe solvent was distilled off
- customAfter leaving the mixture
- waitto stand for several hours
- customcolorless crystals precipitated
Sources & evidence
- ORD record
- ord-08f80c538bca45228c26fd845fb63262
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04254132
Reaction notes
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