Benzocaine → Prop-2-en-1-yl 4-aminobenzoate

HRID 1756419Notes

Reaction equation

HRID 1756419 reaction equation
[Na].[NH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][CH:4]=1.[CH2:14](O)C=C>CCCCCC>[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH:11]=[CH2:14])=[O:8])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 2337BenzocaineHCID 7858Allyl Alcohol2×HCID 5360545Sodium

Product 1

HCID 13075143Prop-2-en-1-yl 4-aminobenzoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

50 ml of allyl alcohol are introduced into a round-bottomed flask, 750 mg (22 mmol) of sodium are added in small portions and the mixture is stirred until the metal has reacted completely. 30.2 g (0.2 mol) of ethyl 4-aminobenzoate, dissolved in 200 ml of allyl alcohol, are then introduced and the mixture is heated to reflux and distilled until 180 ml of distillate have been obtained. The reaction medium is evaporated, the residue is taken up with water and ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is ground in 200 ml of hexane and filtered off. 29 g (82%) of allyl ester, melting point 48°-50° C., are collected.

Workup

  1. customhas reacted completely
  2. additionare then introduced
  3. temperaturethe mixture is heated
  4. temperatureto reflux
  5. distillationdistilled until 180 ml of distillate
  6. customhave been obtained
  7. customThe reaction medium is evaporated
  8. customthe organic phase is separated after settling
  9. dry with materialdried over magnesium sulphate
  10. customevaporated
  11. customThe residue obtained
  12. filtrationfiltered off
  13. custom29 g (82%) of allyl ester, melting point 48°-50° C., are collected

Sources & evidence

ORD record
ord-2a4af5efeead4dd7ba0f924d647d1b86
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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