1-Butanol → n-Butyl-2-(o-phenoxyphenyl)hexanoate

HRID 1613259Notes

Reaction equation

HRID 1613259 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[CH3:6][CH2:7][CH2:8][CH2:9][CH:10]([C:24]#N)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S(=O)(=O)(O)[OH:27]>O>[CH2:1]([O:5][C:24](=[O:27])[CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][CH2:8][CH2:7][CH3:6])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 197756142-(2-Phenoxyphenyl)hexanenitrile

Product 1

HCID 53887059n-Butyl-2-(o-phenoxyphenyl)hexanoateYield 104.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 500-ml round bottom flask are placed 77.7 g (1 mole) of n-butanol, 36.5 g (0.14 mole) of δ-n-butyl o-phenoxybenzyl cyanide and 14.4 g (0.45 mole) of conc. sulfuric acid. The mixture is heated to reflux overnight. It is then cooled, poured into water and extracted with toluene. The combined extracts are washed with water and dried over MgSO4. Solvent is evaporated to give 50 g of product.

Workup

  1. customInto a 500-ml round bottom flask are placed
  2. temperatureThe mixture is heated
  3. temperatureto reflux overnight
  4. temperatureIt is then cooled
  5. extractionextracted with toluene
  6. washThe combined extracts are washed with water
  7. dry with materialdried over MgSO4
  8. customSolvent is evaporated

Sources & evidence

ORD record
ord-a818d85f8fc1464b89e62463d1091a23
Source dataset
uspto-grants-1993_03
Patent number
US05192783

Reaction notes

Loading…