Diethyl Ether → 2-Hydroxy-2-(3-nitrophenyl)acetonitrile
Reaction equation
S(=O)(O)[O-].[Na+].[N+:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])([O-:8])=[O:7].CCOCC.[C-:22]#[N:23].[K+]>O.C1COCC1>[N+:6]([C:9]1[CH:10]=[C:11]([CH:12]([OH:13])[C:22]#[N:23])[CH:14]=[CH:15][CH:16]=1)([O-:8])=[O:7]Participants
7
Conditions
- Temperature
- 10 °C
Procedure
A mixture of a 10% solution of sodium bisulfite (24 g, 230 mmol) and 3-nitrobenzaldehyde (27 g, 178 mmol) was combined in a 1L flask with 75 mL ether and 100 ml THF. The resulting reaction mixture was cooled in an ice-water bath to 10° C. and a solution of potassium cyanide (15 g, 130 mmol) in 75 mL water was added over a period of a half-hour while stirring. The reaction mixture was stirred at 15° C. for 1 hour. The organic layers were separated and the aqueous phase was extracted with ether (200 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford (3-nitrophenyl)(hydroxy)acetonitrile as a yellow oil (29 g, 163 mmol), which was used without further purification in the next step.
Workup
- customThe resulting reaction mixture
- stirringThe reaction mixture was stirred at 15° C. for 1 hour
- customThe organic layers were separated
- extractionthe aqueous phase was extracted with ether (200 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-20ddc5c54e1e426983d49f5ae7b24879
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07528173B2
Reaction notes
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