Acetic Acid → 1-(4-Nitrophenyl)-2-nitro-1,3-propanediol

HRID 2417625Notes

Reaction equation

HRID 2417625 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:12]([CH:15](O)[CH3:16])([O-:14])=[O:13].C(O)(=[O:20])C.Cl>CO.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:8]([OH:9])[CH:15]([N+:12]([O-:14])=[O:13])[CH2:16][OH:20])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 22056827Nitroethanol

Product 1

HCID 134689051-(4-Nitrophenyl)-2-nitro-1,3-propanediolYield 70.24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

7.55 g (0.05 moles) of 4-nitrobenzaldehyde and 4.55 g (0.05 moles) of nitroethanol are suspended in a mixture of 30 ml of methanol and 0.2 ml of triethylamine. The mixture is stirred at 0° C. until dissolution (about 30 minutes) and then allowed to stand at 0° C. for 20 hours. The mixture is acidified (pH 2) with 0.2 ml of acetic acid and 0.2 ml of concentrated hydrochloric acid, and 20 ml of ice-cold water are added. The separated crystals are filtered off, washed with chloroform and dried. 8.5 g (70.24%) of 1-(4-nitrophenyl)-2-nitro-1,3-propanediol are obtained; m.p. 105°-107° C.

Workup

  1. waitto stand at 0° C. for 20 hours
  2. additionare added
  3. filtrationThe separated crystals are filtered off
  4. washwashed with chloroform
  5. customdried

Sources & evidence

ORD record
ord-bc6d5460c6434353ba32bf5d9543c3fd
Source dataset
uspto-grants-1984_09
Patent number
US04469703

Reaction notes

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