Isopropanol → HCID 13042036, compound

HRID 1702517Notes

Reaction equation

HRID 1702517 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[OH-].[K+].[CH:14]([OH:17])([CH3:16])[CH3:15]>O>[CH:14]([O:17][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 12078alpha-Chloro-m-nitrotolueneHCID 14797Potassium Hydroxide

Product 1

HCID 13042036HCID 13042036, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500-milliliter flask equipped with a reflux condenser and a magnetic stirring bar was charged with 17.1 grams (0.1 mole) of 3-nitrobenzyl chloride in 250 milliliters of isopropanol. To this stirred solution was added 6.43 grams (0.1 mole) of potassium hydroxide in 25 milliliters of water. The reaction mixture was heated to reflux and maintained at reflux for 23 hours. The reaction mixture was then cooled, filtered, and the filtrate was concentrated on a rotary evaporator at 55° C. The residue was slurried with 300 milliliters of methylene chloride and transferred to a separatory funnel wherein it was washed consecutively with 100 milliliter portions of 1 Normal hydrochloric acid, water, 1 Normal sodium hydroxide, and water, respectively. The organic phase was separated, dried over magnesium sulfate, and concentrated on a rotary evaporator at 55° C., leaving a dark brown liquid. The dark brown liquid was charged to a distillation flask and distilled at a pressure of 2.4 millimeters of mercury. A main fraction (8.2 grams) was collected, said fraction having a boiling point of 123°-125° C. at 2.4 mm Hg pressure. This main fraction was identified by NMR spectroscopy as 1-(isopropoxymethyl)-3-nitrobenzene.

Workup

  1. customA 500-milliliter flask equipped with a reflux condenser and a magnetic stirring bar
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperaturemaintained
  5. temperatureat reflux for 23 hours
  6. temperatureThe reaction mixture was then cooled
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated on a rotary evaporator at 55° C
  9. customtransferred to a separatory funnel
  10. washwherein it was washed consecutively with 100 milliliter portions of 1 Normal hydrochloric acid, water, 1 Normal sodium hydroxide, and water
  11. customThe organic phase was separated
  12. dry with materialdried over magnesium sulfate
  13. concentrationconcentrated on a rotary evaporator at 55° C.
  14. customleaving a dark brown liquid
  15. additionThe dark brown liquid was charged to a distillation flask
  16. distillationdistilled at a pressure of 2.4 millimeters of mercury
  17. customA main fraction (8.2 grams) was collected

Sources & evidence

ORD record
ord-3e6d529c79cc4f779cdd807c25cfbf37
Source dataset
uspto-grants-1982_09
Patent number
US04348223

Reaction notes

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