p-Toluenesulfonic acid → HCID 20453979, compound

HRID 1462155Notes

Reaction equation

HRID 1462155 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:17](=[O:28])([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[NH2:18]>C(OCC)C>[CH3:3][C:2]([CH3:4])=[CH:1][NH:18][C:17](=[O:28])[O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6561IsobutyraldehydeHCID 16240Carbamic acid, octyl ester

Product 1

HCID 20453979HCID 20453979, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

126 parts of isobutyraldehyde and 7 parts of p-toluenesulfonic acid are added in succession to a solution of 605.5 parts of n-octyl carbamate in 1,750 parts by volume of diethyl ether at 25° C., after which the temperature rises to 40° C. for one hour. After one day, the solid product which as crystallized out is filtered off with suction and fractionally distilled in the presence of 10 parts of p-toluenesulfonic acid and one part of hydroquinone. 298.3 parts of n-octyl N-(2-methyl-1-propenyl)-carbamate (75.1% yield, based on isobutyraldehyde employed) of boiling point 126° C./1 mbar are obtained, and 279.5 parts of n-octyl carbamate are recovered and can be re-used.

Workup

  1. waitAfter one day
  2. customthe solid product which as crystallized
  3. filtrationout is filtered off with suction
  4. distillationfractionally distilled in the presence of 10 parts of p-toluenesulfonic acid and one part of hydroquinone

Sources & evidence

ORD record
ord-93d2a31424864aaa90d7976ce4eac2c4
Source dataset
uspto-grants-1984_07
Patent number
US04459236

Reaction notes

Loading…