Sulfuric Acid → 3,3-Dibutoxy-2-(dibutoxymethyl)propanenitrile

HRID 2412450Notes

Reaction equation

HRID 2412450 reaction equation
[CH2:1]([O:5][CH:6]=[C:7]([CH:10]([O:16][CH2:17][CH2:18][CH2:19][CH3:20])[O:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:8]#[N:9])[CH2:2][CH2:3][CH3:4].[CH3:21][CH2:22][CH2:23][CH2:24][O-:25].[Na+].S(=O)(=O)(O)O>C(O)CCC>[CH2:17]([O:16][CH:10]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:7]([CH:6]([O:25][CH2:24][CH2:23][CH2:22][CH3:21])[O:5][CH2:1][CH2:2][CH2:3][CH3:4])[C:8]#[N:9])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23669364Sodium n-butylateHCID 544234113-Butoxy-2-(dibutoxymethyl)prop-2-enenitrile

Product 1

HCID 133658093,3-Dibutoxy-2-(dibutoxymethyl)propanenitrileYield 277.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

In 100 ml of n-butanol was dissolved 8.49 g (30 mmoles) of 2-n-butoxymethylene-3,3-di-n-butoxypropanenitrile. To the resulting solution was added 0.87 g (9 mmoles) of sodium n-butylate at room temperature, and the mixture was stirred at room temperature for one hour. Then, the reaction mixture was neutralized with a solution of sulfuric acid in butanol and the resulting inorganic salt was removed by filtration. The filtrate was distilled under reduced pressure to obtain 9.10 g (25 mmoles) of 2-di-n-butoxymethyl-3,3-di-n-butoxypropanenitrile as a colorless transparent oil boiling at 170°-175° C./2 mmHg.

Workup

  1. customthe resulting inorganic salt was removed by filtration
  2. distillationThe filtrate was distilled under reduced pressure

Sources & evidence

ORD record
ord-acae1e15b8e04d30ae66f0136d576d93
Source dataset
uspto-grants-1985_01
Patent number
US04492792

Reaction notes

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