Propylene Glycol → HCID 20347326, compound

HRID 972911Notes

Reaction equation

HRID 972911 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:19]([O-:21])=[O:20])[C:11]=1[N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH:7]=[O:8])([O-:3])=[O:2].[CH2:22]([OH:26])[CH:23](O)[CH3:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:24][CH:23]1[CH2:22][O:26][CH:7]([C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:11]([N:12]([CH2:13][CH2:14][CH3:15])[CH2:16][CH2:17][CH3:18])=[C:10]([N+:19]([O-:21])=[O:20])[CH:9]=2)[O:8]1

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 6101p-Toluenesulfonic acidHCID 203473334-(Dipropylamino)-3,5-dinitrobenzaldehyde

Product 1

HCID 20347326HCID 20347326, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 3.0 g. of 3,5-dinitro-4-(dipropylamino)benzaldehyde, 2.0 ml. of 1,2-propanediol, 75 ml. of benzene, and a small amount of p-toluenesulfonic acid was refluxed for about 4 hours, using a Dean-Stark trap to collect the evolved water. The reaction product mixture was cooled and extracted successively with saturated aqueous sodium bicarbonate solution, and brine, and then dried. The drying agent was filtered off and the benzene solution passed through an aluminum oxide column. The eluate was collected and evaporated. A total of 2.2 g. of 4-(4-methyl-1,3-dioxolan-2-yl)-2,6-dinitro-N,N-dipropylaniline was isolated as an oil.

Workup

  1. additionA mixture of 3.0 g
  2. customto collect the evolved water
  3. temperatureThe reaction product mixture was cooled
  4. extractionextracted successively with saturated aqueous sodium bicarbonate solution, and brine
  5. customdried
  6. filtrationThe drying agent was filtered off
  7. customThe eluate was collected
  8. customevaporated

Sources & evidence

ORD record
ord-756e1266b1a34bc6aeee0d99d06f0525
Source dataset
uspto-grants-1977_10
Patent number
US04054439

Reaction notes

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