Reaction equation
C(O[CH2:4][CH2:5][CH2:6][C:7]1(O)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2)C.C(OC(=O)C)(=O)C.[IH:30].II>>[I:30][CH2:4][CH2:5][CH2:6][CH:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[CH:10][C:9]2[CH:18]=[CH:19][CH:20]=[CH:21][C:8]1=2Participants
Conditions
- Temperature
- 65 °C
Procedure
A solution of 9.25 g. (0.0314 mole) of 5-(3-ethoxypropyl)-5-hydroxy-dibenzo[a,d]cycloheptene prepared as above in 45 ml. of acetic anhydride is heated on the steam-bath for 90 minutes then cooled to 65°C. A stream of nitrogen is passed through the solution while 30 ml. of hydriodic acid (sp. gr., 1.5) is added in portions, keeping the temperature below 90°C. The solution develops a dark brown iodine color during the addition. The solution is heated to 80°C. for 30 minutes, then cooled and poured into ice-water. The brown oil that separates is extracted into benzene and the extract washed with water, dilute sodium thiosulfate solution and finally with water. Evaporation of the benzene gives the product 5-(3-iodopropyl)-5H-dibenzo[a,d]cycloheptene as a yellow oil. A sample gives a precipitate with alcoholic silver nitrate solution.
Workup
- customthe temperature below 90°C
- additionduring the addition
- temperatureThe solution is heated to 80°C. for 30 minutes
- temperaturecooled
- extractionThe brown oil that separates is extracted into benzene
- washthe extract washed with water, dilute sodium thiosulfate solution and finally with water
- customEvaporation of the benzene
Sources & evidence
- ORD record
- ord-a239d11b41624253ba5c857b8b30a755
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03981917
Linked notes
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