2-Nitrobenzyl alcohol → o-Nitrobenzyl n-octylcarbamate

HRID 481697Notes

Reaction equation

HRID 481697 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].[CH2:12]([N:20]=[C:21]=[O:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1>[CH2:12]([NH:20][C:21](=[O:22])[O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 119232-Nitrobenzyl alcoholHCID 76616Octyl isocyanate

Product 1

HCID 18695120o-Nitrobenzyl n-octylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

100 mL toluene, 10 g 2-nitrobenzyl alcohol and 11.4 mL octyl isocyanate were introduced into a 200-mL roundbottom flask and heated under reflux for 2 hours under a nitrogen blanket. After cooling, the reaction solution was washed several times with water, and the toluene solution thereby afforded was then dried over sodium sulfate. The sodium sulfate was thereafter filtered off and the solvent was eliminated from the filtrate using a rotary evaporator. The resulting solid was recrystallized twice from hexane to yield 12.5 g ortho-nitrobenzyl n-octylcarbamate as light-yellow, needle-like crystals. mp=70°-71° C. Infrared absorption=3331 cm-1, 1691 cm-1.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours under a nitrogen blanket
  3. temperatureAfter cooling
  4. washthe reaction solution was washed several times with water
  5. customthe toluene solution thereby afforded
  6. dry with materialwas then dried over sodium sulfate
  7. filtrationThe sodium sulfate was thereafter filtered off
  8. customa rotary evaporator
  9. customThe resulting solid was recrystallized twice from hexane

Sources & evidence

ORD record
ord-389217f1b7e94bceb32acccf43f17d7d
Source dataset
uspto-grants-1998_08
Patent number
US05789460

Reaction notes

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