Ethanol → Ethyl 4-(aminomethyl)benzoate

HRID 1005997Notes

Reaction equation

HRID 1005997 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:17](O)[CH3:18]>>[NH2:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:17][CH3:18])=[O:8])=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 436161Ethyl 4-(aminomethyl)benzoate

Procedure

A mixture of 4-aminomethylbenzoic acid (25 g) and concentrated sulphuric acid (25 ml) in ethanol (250 ml) was heated at reflux for 18 hours. The volume of solvent was reduced to a third by evaporation. The residue poured onto ice (500 g) and basified with concentrated aqueous ammonia. The product was extracted with ethyl acetate (3×200 ml) and the extracts dried and evaporated to give ethyl 4-aminomethylbenzoate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe volume of solvent was reduced to a third by evaporation
  4. additionThe residue poured onto ice (500 g)
  5. extractionThe product was extracted with ethyl acetate (3×200 ml)
  6. customthe extracts dried
  7. customevaporated

Sources & evidence

ORD record
ord-9edfdeab9e4a4ebfa21c896d1344b15b
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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