Sulfuric acid magnesium salt (1:1) → HCID 53700305, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([O-])=[O:17])[CH2:11][CH2:10]1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC.C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][OH:17])[CH2:11][CH2:10]1Participants
Conditions
- Temperature
- -65 °C
Procedure
Toluene (450 ml) was added to the above ethyl 2-(4-(1,3-dioxan-2-ylethyl)cyclohexylethanoate (30.2 g, 106 mmol) in a nitrogen gas atmosphere, followed by cooling the mixture down to -65° C., dropwise adding to the solution, a toluene solution of diisobutylaluminum hydride (1.01 mol/l) 120 ml (121 mmol), stirring the mixture at the same temperature for 45 minutes, dropwise adding a saturated aqueous solution of ammonium chloride (33 ml), heating the mixture up to room temperature, adding ether (100 ml) to the reaction solution, stirring the mixture at the temperature for 1.5 hours, adding magnesium sulfate (10 g), stirring the mixture for one hour, filtering off the reaction solution, washing the filtrate with water, drying over magnesium sulfate, and distilling off the solvent, to obtain 2-(4-(1,3-dioxan-2-ylethyl)cyclohexyl)ethanol (22.0 g, 91.5 mmol). Yield: 86.3%.
Workup
- additiondropwise adding to the solution
- temperatureheating the mixture up to room temperature
- stirringstirring the mixture for one hour
- filtrationfiltering off the reaction solution
- washwashing the filtrate with water
- dry with materialdrying over magnesium sulfate
- distillationdistilling off the solvent
Sources & evidence
- ORD record
- ord-22bc3a60191b437e8a863f08cddbe258
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05702641
Reaction notes
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