1-Butanol → Butoxypropionitrile

HRID 1770242Notes

Reaction equation

HRID 1770242 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[OH-].[CH2:7]([N+:14](C)(C)C)[C:8]1C=CC=C[CH:9]=1.C(#N)C=C>C(O)(=O)C>[CH2:1]([O:5][CH:8]([CH3:9])[C:7]#[N:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 7855Acrylonitrile2×HCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 20095850ButoxypropionitrileYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 148 grams (2.0 moles) of n-butanol and 2.0 grams of 40% benzyltrimethylammonium hydroxide (Triton B) is combined in a 1 liter 4-neck round bottom flask stirred at reflux while 106 grams (2.0 moles) of acrylonitrile is added at a rate such that the temperature does not exceed 45° C. The mixture is stirred an hour after all the acrylonitrile has been added, made acidic with acetic acid, and fractionated under vacuum through a Vigreux column. The product boils at 75° C./2 mm (literature value: 98° C./20 mm). The product totalled 188.0 grams of 99.0% pure material which constituted a 74.0% yield. The density of the product was determined to be 0.93 grams/ml. The nuclear magnetic resonance and infrared spectra were obtained and were determined to be consistent with the expected structure of the product.

Workup

  1. customis combined in a 1 liter 4-neck round bottom flask
  2. additionis added at a rate such that the temperature
  3. customdoes not exceed 45° C
  4. additionhas been added
  5. customwere obtained

Sources & evidence

ORD record
ord-11a8f7afd7f94dc1bff785ba96a1d7fe
Source dataset
uspto-grants-1995_01
Patent number
US05385948

Reaction notes

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