Water → 1-(3-Iodophenoxy)-6-(2,4,6-triiodophenoxy)-hexane

HRID 2396412

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1.[I:15][C:16]1[CH:29]=[C:28]([I:30])[CH:27]=[C:26]([I:31])[C:17]=1[O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]Cl.O>CN(C=O)C>[I:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][O:18][C:17]1[C:26]([I:31])=[CH:27][C:28]([I:30])=[CH:29][C:16]=1[I:15]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of potassium carbonate (3.0 g, 21.9 mmol, 1.1 eq), 3-iodophenol (4.4 g, 19.9 mmol) and 6-(2,4,6-triiodophenoxy)-1-chlorohexane (11.75 g, 19.9 mmol) in 50 ml of DMF was heated to 110° C. for 1.5 hours and then cooled. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried (magnesium sulfate) and evaporated to give a solid which was filtered through basic alumina (hexanes-ethyl acetate). The filtrate was concentrated under vacuum leaving the crude product as a solid. Recrystallization from cyclohexane afforded 8.29 g (54%) of the desired product after drying at room temperature under high vacuum, mp 65°-66° C.

Workup

temperaturecooled
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried (magnesium sulfate)
customevaporated
customto give a solid which
filtrationwas filtered through basic alumina (hexanes-ethyl acetate)
concentrationThe filtrate was concentrated under vacuum
customleaving the crude product as a solid
customRecrystallization from cyclohexane

Sources & evidence

ORD record: ord-6abb4f83bc43455e97a87675cd7e5c5e
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05492687

Linked notes

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