Benzaldehyde → HCID 686705, compound

HRID 988006Notes

Reaction equation

HRID 988006 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([CH3:12])([O-:11])=[O:10]>>[C:2]1([C@H:1]([OH:8])[CH2:12][N+:9]([O-:11])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 240BenzaldehydeHCID 6375Nitromethane

Product 1

HCID 686705HCID 686705, compoundYield 84%

Procedure

Further, the present inventors has reported in Tetrahedron Letters (1993) Vol. 34, p. 2657 that the reaction between benzaldehyde and nitromethane under a catalyst of lanthanum-lithium-(R)-binaphthol complex at −50° C. gives (S)-1-phenyl-2 nitro ethanol in a yield of 84% (40% e.e.), and when carried out under a catalyst of samarium-lithium-(R)-binaphthol complex at −40° C., the reaction gives the same compound in a yield of 90% (62% e.e.) ((R) or (S) in the name of leach compound represents R or S isomer, respectively, showing the compound's configuration).

Sources & evidence

ORD record
ord-261705692d6c405ebc21eda6c999ffb8
Source dataset
uspto-grants-2003_10
Patent number
US06632955B1

Reaction notes

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