Formaldehyde → 2-Nitrophenethyl alcohol

HRID 1155208Notes

Reaction equation

HRID 1155208 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].[OH-].[K+]>CN(C)C=O.O>[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

6

Reactant 3

HCID 712FormaldehydeHCID 69442-NitrotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 270542-Nitrophenethyl alcoholYield 41.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 137 g (1 mole) of o-nitrotoluene, 60 g of paraformaldehyde and 400 ml of dimethyl formamide containing 0.5% by weight of water is heated to 70° C. under stirring. Thereafter 40 g of potassium hydroxide, covered with 100 ml dimethyl formamide, are added to the mixture at such a rate that the temperature of the reaction mixture does not increase above 120° C. The resulting mixture is stirred for 3 minutes at a temperature above 85° C., thereafter it is cooled and filtered through a sintered glass filter. The filtrate is acidified with hydrochloric acid to pH=3, filtered again, and the resulting filtrate is evaporated. 100 g of a residue, containing 80% by weight of 2-(o-nitrophenyl)-ethanol, are obtained. This residue is distilled in vacuo to obtain 70 g of 2-(o-nitrophenyl)-ethanol with a purity grade of 98%. 45 g of o-nitrotoluene are recovered. The product is analyzed by gas chromatography.

Workup

  1. additionare added to the mixture at such a rate that the temperature of the reaction mixture
  2. temperaturedoes not increase above 120° C
  3. stirringThe resulting mixture is stirred for 3 minutes at a temperature above 85° C.
  4. temperatureit is cooled
  5. filtrationfiltered through a sintered glass
  6. filtrationfilter
  7. filtrationfiltered again
  8. customthe resulting filtrate is evaporated
  9. addition100 g of a residue, containing 80% by weight of 2-(o-nitrophenyl)-ethanol
  10. customare obtained
  11. distillationThis residue is distilled in vacuo

Sources & evidence

ORD record
ord-46de8f7da7994cb19c050488e38ff5c4
Source dataset
uspto-grants-1981_11
Patent number
US04299992

Reaction notes

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