Methylparaben → Methyl 4-(2-aminoethoxy)benzoate

HRID 1762171Notes

Reaction equation

HRID 1762171 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1)=[O:4].[NH:12]1[CH2:14][CH2:13]1>C(Cl)(Cl)Cl>[NH2:12][CH2:13][CH2:14][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7456MethylparabenHCID 9033Aziridine

Product 1

HCID 14097616Methyl 4-(2-aminoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl p-hydroxybenzoate (7.6 g) was dissolved in 50 ml of chloroform with heating, 2.15 g of aziridine was dropped in with stirring, and the mixture was heated to refluxed for 8 hours. The reaction solution was concentrated in vacuo and the residue was purified by a silica gel column chromatography (200 g of silica gel C-200; the eluting solvent used was a 9:1 mixture of chloroform and methanol).

Workup

  1. temperaturewith heating
  2. temperaturethe mixture was heated
  3. temperatureto refluxed for 8 hours
  4. concentrationThe reaction solution was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (200 g of silica gel
  6. additiona 9:1 mixture of chloroform and methanol)

Sources & evidence

ORD record
ord-4014ca8cd0cd4fe9b72eec63e054aef5
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

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