Methanol → Methyl 4-(aminomethyl)benzoate

HRID 1174504Notes

Reaction equation

HRID 1174504 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(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:8][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([CH2:2][NH2:1])=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 655264-(Aminomethyl)Benzoic Acid

Product 1

HCID 571728Methyl 4-(aminomethyl)benzoateYield 92%

Procedure

To a solution of 4-(aminomethyl)benzoic acid (300 g, 1.98 mol) in methanol (5 L) was added thionylchloride (473 g 3.97 mol). The reaction mixture was refluxed for 6 h, followed by the removal of the solvent under reduced pressure to obtain the crude product. The crude was purified by acid-base work up to afford methyl-4-(aminomethyl)benzoate (300 g, 92%) as a liquid.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. customfollowed by the removal of the solvent under reduced pressure
  3. customto obtain the crude product
  4. customThe crude was purified by acid-base work up

Sources & evidence

ORD record
ord-9e32ca7ba0c14e728d74911ef8233737
Source dataset
uspto-grants-2010_11
Patent number
US07838522B2

Reaction notes

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