Sulfuric Acid → 5-(2,6-Dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone

HRID 1280246

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

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-aa0eaf858e9b47c080cf5c256cb6c62b
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448444B1

Linked notes

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