Sulfuric Acid → tert-Butylacrylamide

HRID 1608003Notes

Reaction equation

HRID 1608003 reaction equation
[C:1](#[N:4])[CH:2]=[CH2:3].[C:5](O)([CH3:8])([CH3:7])[CH3:6].S(=O)(=O)(O)[OH:11]>C(O)(=O)C>[C:5]([NH:4][C:1](=[O:11])[CH:2]=[CH2:3])([CH3:8])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 7855Acrylonitrile

Product 1

HCID 7877tert-ButylacrylamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of acrylonitrile (5.3 g), tert-butyl alcohol (7.4 g) and acetic acid (50 ml), cooled in an ice-bath, was added dropwise concentrated sulfuric acid (10.1 g, 97%) at a temperature below 40° C. The mixture was held at 40° C. for 1 hour and then poured into 200 g of ice water with constant stirring. The precipitate was filtered, washed with water and dried to afford N-tert-butylacrylamide (10.3 g, 82.4%); m.p. 124°-6° C.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-cf61938c310f4a0ab931698d36035faa
Source dataset
uspto-grants-1989_09
Patent number
US04868310

Reaction notes

Loading…