Sulfuric Acid → 5-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][CH:16]=[CH2:17].S(=O)(=O)(O)[OH:26]>S([O-])([O-])(=O)=O.[Hg+2].O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([O:19][CH2:20][CH:21]=[C:22]([Cl:24])[Cl:23])[CH:5]=[C:6]([Cl:18])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16](=[O:26])[CH3:17]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 4.12 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(5-(2-propenyloxy)pentyloxy)benzene, 0.36 g of mercury (II) sulfate, 5 ml of 1% aqueous sulfuric acid solution, and 50 ml of tetrahydrofuran was stirred at 60° C. for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was poured into diluted hydrochloric acid, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with diluted hydrochloric acid and water in this order, dried over magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 4.05 g (yield, 94%) of 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone, nD25.5 1.5350.
Workup
- filtrationThe reaction mixture was filtered through Celite
- additionthe filtrate was poured into diluted hydrochloric acid
- extractionextracted twice with diethyl ether
- washwashed with diluted hydrochloric acid and water in this order
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customto give a crude product
Sources & evidence
- ORD record
- ord-6a9565bda415462682461a0bd23a8ff1
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06437184B1
Reaction notes
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