5,6,7,8-Tetrahydro-2-naphthol → 1-Iodo-5,6,7,8-tetrahydro-2-naphthol
Reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[I:12]Cl>C(O)(=O)C>[I:12][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].[I:12][C:3]1[C:2]([OH:11])=[CH:1][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1Participants
Reactant 2
Product 2
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A 4.45 g solution of 5,6,7,8-tetrahydro-2-naphthol was dissolved in 25 ml of glacial acetic acid, mixed with 5.85 g of iodine monochloride and heated under reflux at 100° C. for 2 hours. After reaction, the reaction mixture was poured onto 100 ml of ice water and extracted with ethyl acetate. The extract was washed sequentially with an aqueous solution of sodium thiosulfate (hypo), water and saturated aqueous NaCl solution, dried with anhydrous magnesium sulfate, and concentrated under vacuum. The residue was purified by column chromatography on silica gel using an eluting agent comprising a mixture (1:2) of methylene chloride and cyclohexane to provide white crystals each comprising 2.11 g of 1-iodo-5,6,7,8-tetrahydro-2-naphthol and 2.84 g of 3-iodo-5,6,7,8-tetrahydro-2-naphthol having the following physical properties.
Workup
- temperatureheated
- customAfter reaction
- extractionextracted with ethyl acetate
- washThe extract was washed sequentially with an aqueous solution of sodium thiosulfate (hypo), water and saturated aqueous NaCl solution
- dry with materialdried with anhydrous magnesium sulfate
- concentrationconcentrated under vacuum
- customThe residue was purified by column chromatography on silica gel using an eluting agent
Sources & evidence
- ORD record
- ord-301da0f2579244539b68f36fb430317c
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04254056
Reaction notes
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