3-Nitrobenzaldehyde → 2-Hydroxy-2-(3-nitrophenyl)acetonitrile
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].S(=O)(O)[O-].[Na+].[C-:17]#[N:18].[K+]>CCOCC>[OH:8][CH:7]([C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[C:17]#[N:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 10 °C
Procedure
A mixture of m-nitrobenzaldehyde (27.0 g, 178.7 mmol) and a 10% solution of 24 g of sodium bisulfite was placed in a 2 liter flask and 75 mL of ether was added. The resulting mixture was cooled in an ice-bath to 10° C. and potassium cyanide (15.0 g, 230.3 mmol) in a 20% solution was added over a period of 30 minutes. The mixture was stirred for another 30 minutes after the addition of the potassium cyanide. The ether layer was separated and the aqueous layer was extracted with ether. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to afford 27.81 g (87%) of α-hydroxy-3-nitrobenzeneacetonitrile, a compound of formula (Q), as a pale yellow oil.
Workup
- customThe ether layer was separated
- extractionthe aqueous layer was extracted with ether
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b5e0dd8d9592477aa78d153a83cf1010
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008325B2
Reaction notes
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