2-Nitrobenzyl alcohol → HCID 89852854, compound

HRID 1505831Notes

Reaction equation

HRID 1505831 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[C:12]([O:17][CH2:18][CH2:19][N:20]=[C:21]=[O:22])(=[O:16])[C:13]([CH3:15])=[CH2:14].[N-]=C=O>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1(C)C=CC=CC=1>[CH3:15][C:13](=[CH2:14])[C:12]([O:17][CH2:18][CH2:19][NH:20][C:21]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])=[O:22])=[O:16]

Participants

6

Reactant 3

HCID 119232-Nitrobenzyl alcoholHCID 354092-Isocyanatoethyl methacrylateHCID 105034Isocyanate

Product 1

HCID 89852854HCID 89852854, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 1140TolueneSolvent

Procedure

A composition was prepared by mixing 14.4 g (94 mmol) of 2-nitrobenzyl alcohol (Alfa Aesar; Ward Hill, Mass.), 14.6 g (94 mmol) of isocyanatoethyl methacrylate (Aldrich; Milwaukee, Wis.) and 1 drop of dibutyltin dilaurate (Alfa Aesar) in a 4 ounce glass jar. The jar was sealed and placed in an oven set at 70° C. for 2 hours. Analysis of the reaction mixture by infrared (IR) spectroscopy (Nexus 670 FT-IR E.S.P., Thermo Nicolet Corp.; Madison, Wis.) showed no absorbance at 2250 cm−1, indicating substantially no remaining isocyanate functionality. To the cooled reaction mixture were added 40 mL of toluene and the jar was placed in a refrigerator overnight. The next day, white crystals that had formed were filtered off and dried to provide 26.9 g of 2-({[(2-nitrobenzyl)oxy]carbonyl}amino)ethyl 2-methylacrylate (NBMA). The structure of the product was confirmed by NMR and IR spectroscopy analyses.

Workup

  1. customA composition was prepared
  2. customThe jar was sealed
  3. customplaced in an oven
  4. customTo the cooled reaction mixture
  5. customwas placed in a refrigerator overnight
  6. customThe next day, white crystals that had formed
  7. filtrationwere filtered off
  8. customdried

Sources & evidence

ORD record
ord-4bf65bc1eb644409987550a300822b60
Source dataset
uspto-grants-2015_12
Patent number
US09217050B2

Reaction notes

Loading…