Acetic Acid → 1-(3,4-Dimethoxyphenyl)-2-nitropropane-1,3-diol

HRID 2417623Notes

Reaction equation

HRID 2417623 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[N+:13]([CH:16](O)[CH3:17])([O-:15])=[O:14].C(Cl)(Cl)Cl.C(O)(=[O:25])C>C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[CH:16]([N+:13]([O-:15])=[O:14])[CH2:17][OH:25])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 8419VeratraldehydeHCID 22056827Nitroethanol

Product 1

HCID 134689041-(3,4-Dimethoxyphenyl)-2-nitropropane-1,3-diolYield 74.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Conditions

Temperature
5 °C

Procedure

83.1 g (0.5 moles) of 3,4-dimethoxybenzaldehyde are suspended in 45.5 g (0.5 moles) of nitroethanol in the presence of 2.5 ml of triethylamine catalyst, and the mixture is stirred at 5° C. on an ice-water bath for 5.5 hours. 30 ml of chloroform are added to the reaction mixture in small portions within 5 hours. The mixture is allowed to stand for 12 hours under cooling and then acidified with 2 ml of acetic acid. The separated crystals are filtered off, washed with chloroform and ice-cold water and dried. 96.1 g (74.7%) of 1-(3,4-dimethoxyphenyl)-2-nitro-1,3-propanediol are obtained; m.p.: 134°-138° C.

Workup

  1. waitto stand for 12 hours
  2. temperatureunder cooling
  3. filtrationThe separated crystals are filtered off
  4. washwashed with chloroform and ice-cold water
  5. customdried

Sources & evidence

ORD record
ord-8167f5cb01c843d2bc992479d636414a
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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