Benzaldehyde → 2-nitro-1-phenylethanol

HRID 1912223Notes

Reaction equation

HRID 1912223 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]>[Pd]>[N+:9]([CH2:12][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[OH:8])([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 6375Nitromethane

Product 1

HCID 2268302-nitro-1-phenylethanol

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 250 mm-long tube filled with 3600 mg of pellets (72 pellets, each weighing 50 mg were used, the supported palladium being 0.85 mol % with respect to the reactive substrate) was used as a microreactor. A mixture obtained by mixing 2.1 g (20 mmol) of benzaldehyde and 1.2 g (20 mmol) of nitromethane was filled in a gas tight syringe, and the reaction was conducted at a temperature of 60° C. The flow rate was set to 2.2 ml/h and the retention time was set to 1 hour. After analyzing the resulting product by 1H-NMR, it was confirmed that the inversion rate was 18%, and the objective substance of 2-nitro-1-phenyl-ethanol was approximately obtained quantitatively.

Workup

  1. additionA 250 mm-long tube filled with 3600 mg of pellets (72 pellets
  2. customA mixture obtained
  3. additionwas filled in a gas tight syringe
  4. customwas conducted at a temperature of 60° C

Sources & evidence

ORD record
ord-1f16ee15ccf84e2f80ad0dc5ce7038dd
Source dataset
uspto-grants-2013_12
Patent number
US08609034B2

Reaction notes

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