Ethylene Glycol → (1-Allylcyclohexyl)benzene
Reaction equation
[CH2:1]([C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][C:5]1=O)[CH:2]=[CH2:3].C(O)CO.NN.[OH-].[K+]>>[CH2:1]([C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3]Participants
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-allyl-2-phenylcyclohexanone (1.97 g, 9.19 mmol) in ethylene glycol (8 mL, 143 mmol) were added hydrazine (0.8 mL, 25 5 mmol) and potassium hydroxide (1.547 g, 27 6 mmol), and the mixture was stirred at 100° C. for 1 hr and refluxed in a 180° C. oil bath for 2.5 hrs. TLC showed that the hydrazone formation nearly complete. Then the excess hydrazine and water were distilled out in a 200° C. oil bath, and it was continued to heat at the same temperature for 4 hrs. After cooling to room temperature, the mixture was added to ether and washed with water and brine. The combined aqueous layers were back-extracted with ether (2×), combined, dried over Na2SO4, and evaporated to give an oily residue. It was purified by Combiflash (80 g silica gel) eluting with hexane followed by 5:95 EtOAc-hexane to give product (825 mg).
Workup
- temperaturerefluxed in a 180° C. oil bath for 2.5 hrs
- distillationThen the excess hydrazine and water were distilled out in a 200° C. oil bath
- temperatureto heat at the same temperature for 4 hrs
- temperatureAfter cooling to room temperature
- additionthe mixture was added to ether
- washwashed with water and brine
- extractionThe combined aqueous layers were back-extracted with ether (2×)
- dry with materialdried over Na2SO4
- customevaporated
- customto give an oily residue
- customIt was purified by Combiflash (80 g silica gel)
- washeluting with hexane
Sources & evidence
- ORD record
- ord-e1827ae244e1486086eafa58fe5d63d1
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187437B2
Reaction notes
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