Diethyl Ether → HCID 20442396, compound
Reaction equation
[C:1]([O-:4])([O-])=[O:2].[C:5]([O-:8])([O-])=O.O.O.O.[K+].[K+].[K+].[K+].[N+]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N+:33]([O-:35])=[O:34])=[O:26])([O-])=O.[C:36](=[O:39])([O-])[O-].[K+].[K+].[BH4-].[Na+].[CH3:44][CH2:45]OCC>O>[N+:33]([C:28]1[CH:29]=[C:30]([O:39][CH3:36])[C:31]([O:8][CH3:5])=[CH:32][C:27]=1[CH:25]([OH:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:19][CH2:44][CH2:45][C:1]([OH:4])=[O:2])([O-:35])=[O:34]Participants
7
Procedure
To a rapidly stirred solution of 8.33 g potassium carbonate 1.5 hydrate in 330 ml water was added 18.5 g of the nitrophenyl ketone. 2.5 g of potassium carbonate was added to make a clear solution. A solution of 2.36 g sodium borohydride in 50 ml water was added over 5 min. The mixture was heated to 45° for one hour, cooled to room temperature over 2 hours, and shaken with 200 ml ether. The layers were separated and the water layer stirred as a solution of 8% aqueous HCl was added until the solution was a pH of 2-3. An orange solid was collected by filtration, blended in ice water, filtered, washed with water and vacuum oven dried at 60° C. to yield 18 g, 95% yield.
Workup
- temperatureThe mixture was heated to 45° for one hour
- customThe layers were separated
- additionwas added until the solution
- filtrationAn orange solid was collected by filtration
- filtrationfiltered
- washwashed with water and vacuum oven
- customdried at 60° C.
- customto yield 18 g, 95% yield
Sources & evidence
- ORD record
- ord-102b56ac825d4f15b61d0034a5d2058e
- Source dataset
- uspto-grants-1984_10
- Patent number
- US04477556
Reaction notes
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