Resorcinol → 4,6-Bis(adamantyl)resorcinol
Reaction equation
[C:1]12(O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[C:24]1([CH:31]=[CH:30][CH:29]=[C:27]([OH:28])[CH:26]=1)[OH:25].[CH3:32][CH2:33][CH2:34]CCCC>>[C:1]12([C:29]3[CH:30]=[C:31]([C:13]45[CH2:18][CH:17]6[CH2:32][CH:33]([CH2:34][CH:15]([CH2:16]6)[CH2:14]4)[CH2:23]5)[C:24]([OH:25])=[CH:26][C:27]=3[OH:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2Participants
Procedure
A 500 mL four-necked flask equipped with a reflux condenser, a stirrer, a thermometer, and a nitrogen inlet tube was charged with 28.1 g (0.18 mol) of 1-adamantanol, 15.84 g (0.09 mol) of p-toluenesulfonic acid monohydrate, and 300 mL of heptane and replaced with nitrogen. The mixture was added with 9.9 g (0.09 mol) of resorcinol. The flask was immersed in an oil bath at 100° C. and the mixture was heated while stirring for 1 hour. After cooling the reaction mixture, the solid content was collected by filtration, which was then dried under vacuum, followed by recrystallization by aqueous methanol solution to obtain 4,6-bis(1-adamantyl)-1,3-dihydroxybenzene (yield: 86%, LC (liquid chromatography) purity: 99.7%, melting point: 146° C.). Note that the LC purity was measured by absorbance at λ=280 nm.
Workup
- customA 500 mL four-necked flask equipped with a reflux condenser, a stirrer
- customThe flask was immersed in an oil bath at 100° C.
- temperaturethe mixture was heated
- temperatureAfter cooling the reaction mixture
- filtrationthe solid content was collected by filtration, which
- customwas then dried under vacuum
- customfollowed by recrystallization by aqueous methanol solution
Sources & evidence
- ORD record
- ord-17ef810131f149b38af4d8946e8d6533
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08110614B2
Reaction notes
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