Sodium Hydroxide → HCID 12798027, compound

HRID 1106023Notes

Reaction equation

HRID 1106023 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:21]([CH3:23])[CH3:22])[C:11]([O:13]CC2C=CC=CC=2)=[O:12])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].O1CCOCC1.[OH-].[Na+]>O>[N:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:21]([CH3:23])[CH3:22])[C:11]([OH:13])=[O:12])=[CH:8][CH:9]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 12798026HCID 12798026, compound

Product 1

HCID 12798027HCID 12798027, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of 2-(4-azidophenyl)-3-methylbutanoic acid, benzyl ester, 25 ml of dioxane, 10 ml of water and 5.2 g of 50% sodium hydroxide was stirred and boiled under reflux for 30 hours. Most of the dioxane was evaporated in vacuum, and the oily residue diluted with water and butyl chloride, and acidified with 4 N HCl. The butyl chloride solution was washed with water (2 times) and saturated brine, dried (MgSO4), and evaporated to a residual oily solid. Stirring with hexane provided 4.3 g of 2-(4-azidophenyl)-3-methylbutanoic acid as a yellowish solid, m.p. 95°-97°. The infrared spectrum shows absorption peaks at 2120 cm-1 (azide) and 1715 cm-1 (carboxylic acid carbonyl).

Workup

  1. temperatureunder reflux for 30 hours
  2. customMost of the dioxane was evaporated in vacuum
  3. additionthe oily residue diluted with water and butyl chloride
  4. washThe butyl chloride solution was washed with water (2 times) and saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a residual oily solid
  7. stirringStirring with hexane

Sources & evidence

ORD record
ord-2f4efe38a14149ac951bf3702690082c
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

Loading…