p-Toluenesulfonic acid → HCID 54435613, compound

HRID 1462156Notes

Reaction equation

HRID 1462156 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH:5]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:18](=[O:22])([O:20][CH3:21])[NH2:19]>C(OCC)C>[CH:5]([NH:19][C:18](=[O:22])[O:20][CH3:21])=[CH:4][CH2:3][CH2:2][CH3:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8063PentanalHCID 11722Methyl Carbamate

Product 1

HCID 54435613HCID 54435613, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

430 parts of n-valeraldehyde and 5 parts of p-toluenesulfonic acid are added in succession to a solution of 750 parts of methyl carbamate in 2,000 parts by volume of diethyl ether at 25° C. After a reaction time of one hour, in which the temperature rises to 40° C., filtration with suction and subsequent fractional distillation of the solid in the presence of 15 parts of potassium carbonate and 2 parts of hydroquinone give 559.1 parts of methyl N-(1-pentenyl)-carbamate (78.2% yield, based on n-valeraldehyde employed) as a cis/trans isomer mixture of boiling point 97°-102° C./16 mbar, and 352.5 parts of methyl carbamate, which can be re-used.

Workup

  1. customAfter a reaction time of one hour
  2. customrises to 40° C.
  3. filtrationfiltration
  4. distillationwith suction and subsequent fractional distillation of the solid in the presence of 15 parts of potassium carbonate and 2 parts of hydroquinone

Sources & evidence

ORD record
ord-3ce75429ffc64a2497bf807c09b3cfef
Source dataset
uspto-grants-1984_07
Patent number
US04459236

Reaction notes

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