Glycerol → HCID 20074437, compound

HRID 1031320Notes

Reaction equation

HRID 1031320 reaction equation
[OH-].[K+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([N+:12]([O-:14])=[O:13])=[CH:6][C:5]=2[O:4]1.O.[OH:16][CH2:17][CH:18](CO)[OH:19]>>[OH:4][C:5]1[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][C:10]=1[O:11][CH2:3][CH:18]([OH:19])[CH2:17][OH:16]

Participants

5

Reactant 4

HCID 753GlycerolHCID 962WaterHCID 14797Potassium HydroxideHCID 757981,3-Benzodioxole, 5-nitro-

Product 1

HCID 20074437HCID 20074437, compound

Conditions

Temperature
110 °C

Procedure

0.3 mol (19.8 g) of 85% by weight potassium hydroxide pellets is dissolved in 210 ml of glycerol, and 0.25 mol (41.75 g) of 3,4-methylenedioxynitrobenzene is then added, with stirring. After heating for one and a half hours in the region of 110° C., the reaction medium is poured into 1.5 litres of iced water. The mixture is filtered in order to remove a small quantity of starting material. The filtrate is acidified to pH=4 with hydrochloric acid and then treated with 10 g of vegetable charcoal. After stirring for a few minutes at ambient temperature and removal of the vegetable charcoal by filtration, the solution is left to stand overnight at 0° C. and the expected product which has crystallized is then filtered off. After recrystallization from ethanol and drying in vacuo, the product melts at 148° C.

Workup

  1. filtrationThe mixture is filtered in order
  2. customto remove a small quantity of starting material
  3. additiontreated with 10 g of vegetable charcoal
  4. stirringAfter stirring for a few minutes at ambient temperature
  5. customremoval of the vegetable charcoal
  6. filtrationby filtration
  7. waitthe solution is left
  8. customthe expected product which has crystallized
  9. filtrationis then filtered off
  10. customAfter recrystallization from ethanol
  11. customdrying in vacuo

Sources & evidence

ORD record
ord-4503d509850c45ff894fa9e1c5ff28b8
Source dataset
uspto-grants-1990_09
Patent number
US04954131

Reaction notes

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