p-Toluenesulfonic acid → HCID 86666522, compound

HRID 1397106Notes

Reaction equation

HRID 1397106 reaction equation
[NH:1]([CH2:6][C:7]([OH:9])=[O:8])[CH2:2][C:3]([OH:5])=[O:4].[CH2:10](O)[CH:11]=[CH2:12].[C:14]1(C)[CH:19]=CC(S(O)(=O)=O)=C[CH:15]=1>C1C=CC=CC=1>[C:3]([O:5][CH2:19][CH:14]=[CH2:15])(=[O:4])[CH2:2][NH:1][CH2:6][C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7858Allyl AlcoholHCID 8897Iminodiacetic acid

Product 1

HCID 86666522HCID 86666522, compoundYield 170.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of iminodiacetic acid 8 (3.0 g, 22.54 mmol), allyl alcohol (18.43 mL, 270 mmol) and p-toluenesulfonic acid (8.57 g, 45.0 mmol) in benzene (60 mL) was heated at reflux with a Dean-Stark distilling trap for 16 h. The mixture was cooled to room temperature and the solvent was evaporated in vacuo. The residue was crystallized from diethyl ether and dried in vacuo to give the compound 9 (8.21 g, 94.6%). 1H NMR (400 MHz, CDCl3) δ 2.34 (s, 3H), 4.17 (s, 4H), 4.61 (d, J=6.2, 4H), 5.24 (d, J=11.7, 2H), 5.31 (d, J=17.2, 2H), 5.82 (m, 2H), 7.15 (d, J=7.8, 2H), 7.68 (d, J=8.2, 2H).

Workup

  1. temperatureat reflux with a Dean-Stark
  2. distillationdistilling trap for 16 h
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was crystallized from diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2b5e3cde4e384ed8915fc9e982dd4167
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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