Hydrochloric Acid → 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde O-propyloxime
Reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:16]=[C:15]([Cl:25])[C:3]=1[O:4][CH2:5][CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.Cl.[CH2:27]([O:30][NH2:31])[CH2:28][CH3:29].Cl>N1C=CC=CC=1>[CH2:27]([O:30][N:31]=[CH:11][C:10]1[CH:13]=[CH:14][C:7]([CH2:6][CH2:5][O:4][C:3]2[C:2]([Cl:1])=[CH:18][C:17]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])=[CH:16][C:15]=2[Cl:25])=[CH:8][CH:9]=1)[CH2:28][CH3:29]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 0.55 g of 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde (which had been produced in Intermediate Production Example 3 as described below) and 5 ml of pyridine was added 0.18 g of O-propylhydroxylamine hydrochloride. After stirring at room temperature for 24 hours, the reaction mixture was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 0.45 g (yield, 72%) of 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde O-propyloxime, m.p., nD24.5 1.5773.
Workup
- extractionextracted twice with diethyl ether
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customto give a crude product
Sources & evidence
- ORD record
- ord-85337a69beb8481281794d30aadfb6c3
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06448444B1
Reaction notes
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