Sodium Hydroxide → Benzenamine, 3-ethynyl-

HRID 1855880Notes

Reaction equation

HRID 1855880 reaction equation
CC(O)([C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH2:12][C:8]1[CH:7]=[C:6]([C:5]#[CH:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1122363-Butyn-2-ol, 4-(3-aminophenyl)-2-methyl-

Product 1

HCID 104682Benzenamine, 3-ethynyl-Yield 104.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 grams of 2-methyl-4-(3-aminophenyl)-3-butyn-2-ol were dissolved in 15 ml of toluene containing one pellet (0.1 grams) of sodium hydroxide which had been crushed to a powder. The mixture was charged to a 100 ml, round-bottom flask equipped with a Dean-Stark trap and condenser. The mixture was refluxed for one hour, and the accetone byproduct was removed periodically through the Dean-Stark trap. The reaction product was then cooled, and the mixture filtered to remove particles of caustic. After the solvent was stripped, a quantitative yield of 3-aminophenylacetylene (1.4 grams) of greater than 98% purity as analyzed by gas chromatography was obtained; refractive index, nD20, 1.686.

Workup

  1. customhad been crushed to a powder
  2. additionThe mixture was charged to a 100 ml, round-bottom flask
  3. customequipped with a Dean-Stark trap and condenser
  4. temperatureThe mixture was refluxed for one hour
  5. customthe accetone byproduct was removed periodically through the Dean-Stark trap
  6. temperatureThe reaction product was then cooled
  7. filtrationthe mixture filtered
  8. customto remove particles of caustic

Sources & evidence

ORD record
ord-c9aa5bcf0752448787e3d611a0a62870
Source dataset
uspto-grants-1980_08
Patent number
US04216341

Reaction notes

Loading…