Reacción #598891

ord-72b3247e66d848a196170708dc54c402

Ecuación de reacción

O=C(O)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
3,5-dinitrobenzoic acid
O=C([O-])O.[Na+]
sodium hydrogen carbonate
[I-].[Na+]
sodium iodide
OCCCCCCCl
6-chlorohexanol
O=C(OCCCCCCO)c1cc([N+](=O)[O-])cc([N+](=O)[O-])c1
6-hydroxyhexyl 3,5-dinitrobenzoate
Rendimiento 91.0%

Condiciones de reacción

Temperatura
50°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathe mixture is heated up to 90° C
  2. 2
    Temperaturais heated to 100° C. for 1 h
  3. 3
    OtroAfter 1 h of reaction
  4. 4
    FiltraciónThe product is filtrated
  5. 5
    Lavadowashed water
  6. 6
    Otrodried at 50° C. under vacuum for 24 h

Procedimiento

357.70 g (1.686 Mol) of 3,5-dinitrobenzoic acid is suspended in 750 ml of 1-methyl-2-pyrrolidone. The suspension is stirred up to 50° C. 386.36 g (4.599 Mol) of sodium hydrogen carbonate are added and the mixture is heated up to 90° C. 22.50 g (0.150 Mol) of sodium iodide and 204.0 ml (1.533 Mol) of 6-chlorohexanol are added to the reaction mixture which is heated to 100° C. for 1 h. After 1 h of reaction, the reaction is complete and the orange suspension is thrown on 2 l of ice and 1 l of water. The product is filtrated, washed water and dried at 50° C. under vacuum for 24 h to give 425.0 g (91%) of 6-hydroxyhexyl 3,5-dinitrobenzoate as a rose powder.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09097938B2uspto-grants-2015_08