Cerium(III) chloride → 2-Nitrocinnamyl alcohol

HRID 1106934Notes

Reaction equation

HRID 1106934 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1/[CH:8]=[CH:9]/[CH:10]=[O:11])([O-:5])=[O:4].[Cl-].[Ce+3].[Cl-].[Cl-].[NH4+].[Cl-]>CO>[N+:3]([C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[CH:8]=[CH:9][CH2:10][OH:11])([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 24636Cerium(III) chlorideHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 53671222-Nitrocinnamaldehyde

Product 1

HCID 533957172-Nitrocinnamyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (1.15 g, 31.1 mmol) was added portionwise to an ice cooled suspension of trans-2-nitrocinnamaldehyde (5.00 g, 28.2 mmol), and cerium (III) chloride (12.61 g, 33.8 mmol) in methanol (140 ml). After stirring at room temperature for 30 minutes the mixture was poured into saturated aqueous NH4Cl (200 ml), extracted with DCM (3×150 ml) and the extacts dried (MgSO4). Filtration and evaporation of the solvent gave the product. (5.03 g, 100%)

Workup

  1. temperaturecooled
  2. extractionextracted with DCM (3×150 ml)
  3. dry with materialthe extacts dried (MgSO4)
  4. filtrationFiltration and evaporation of the solvent
  5. customgave the product

Sources & evidence

ORD record
ord-7f8e6c8452c7405fa345d8c5a83e6fdb
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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