Hydrochloric Acid → 6-[((2E)-{4-hydroxyphenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate

HRID 1042610Notes

Reaction equation

HRID 1042610 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[C:34]([N+:36]([O-:38])=[O:37])[CH:35]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:32])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([O:26]C(OCC)=O)=[CH:22][CH:21]=1)=[O:8])([O-:3])=[O:2].N1C=CC=CC=1.[OH-].[NH4+].Cl>CC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:33]=[C:34]([N+:36]([O-:38])=[O:37])[CH:35]=1)[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C:17](=[O:32])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14923Ammonium HydroxideHCID 598504176-[((2E)-{4-[(ethoxycarbonyl)oxy]phenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate

Product 1

HCID 598504266-[((2E)-{4-hydroxyphenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoateYield 42.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

43.20 g (0.081 Mol) of 6-[((2E)-{4[(ethoxycarbonyl)oxy]phenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate are dissolved in 66 ml (0.815 Mol) of pyridine and 400 ml of acetone at room temperature. 61 ml (0.815 Mol) of ammonium hydroxide solution 25% are added dropwise to the solution at room temperature. After 12h reaction, the mixture is thrown on water and acidified by the addition of HCl 25% (up to pH=3-4). A paste is obtained which is filtrated and dissolved in ethyl acetate and extracted with water. The organic phase is dried with sodium sulfate, filtrated, concentrated by rotary evaporation. Filtration of the residue over silica gel with tert-Butyl methyl ether as eluant and crystallization of the residue in 200 ml of ethyl acetate and 1200 ml of hexane at 0° C. give 15.84 g of 6-[((2E)-{4-hydroxyphenyl}prop-2-enoyl)oxy]hexyl 3,5-dinitrobenzoate as yellow crystals.

Workup

  1. customat room temperature
  2. customA paste is obtained which
  3. filtrationis filtrated
  4. dissolutiondissolved in ethyl acetate
  5. extractionextracted with water
  6. dry with materialThe organic phase is dried with sodium sulfate
  7. filtrationfiltrated
  8. concentrationconcentrated by rotary evaporation
  9. filtrationFiltration of the residue over silica gel with tert-Butyl methyl ether as eluant
  10. customcrystallization of the residue in 200 ml of ethyl acetate

Sources & evidence

ORD record
ord-8cb4653171494fb5bbbe6da17bde0001
Source dataset
uspto-grants-2013_10
Patent number
US08557922B2

Reaction notes

Loading…