Formaldehyde → 2-Nitrophenethyl alcohol

HRID 963747Notes

Reaction equation

HRID 963747 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-:3])=[O:2].[CH2:11]=[O:12]>CS(C)=O.[OH-].[K+]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][OH:12])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 69442-Nitrotoluene

Product 1

HCID 270542-Nitrophenethyl alcoholYield 55.8%

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

KOH (21 mg, 0.37 mmol) was added to a mixture of o-nitrotoluene (9.2 g, 67 mmol) and paraformaldehyde (0.8 g, 25 mmol) in DMSO (10 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å) which was then stirred for 2.5 h at 95° C. The solvent was removed and the residue purified by column chromatography (SiO2, 20×3 cm, solvent: toluene 750 ml, toluene/EtOAc 10:1 500 ml, 7:1 500 ml, 5:1 500 ml). 2-(2-nitrophenyl)ethanol (2.33 g, 21%) was obtained as a yellow oil.

Workup

  1. custom10 ml, synthesis quality
  2. customadditionally dried for 2 d over molecular sieve 4 Å) which
  3. customThe solvent was removed
  4. customthe residue purified by column chromatography (SiO2, 20×3 cm, solvent: toluene 750 ml, toluene/EtOAc 10:1 500 ml, 7:1 500 ml, 5:1 500 ml)

Sources & evidence

ORD record
ord-f0a102f5d8dd41bb8cbe6159c3a8c722
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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