Caprolactam → p-Toluenesulfonic acid

HRID 589545Notes

Reaction equation

HRID 589545 reaction equation
C1(=O)NCCCCC1.O.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1>>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7768Caprolactam2×HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acid

Procedure

In a 20 mL vial, 1.05 g (9.2 mmol) of caprolactam was melted at 80° C. with stirring. p-toluene sulfonic acid monohydrate (9.0 mmol) was added to the caprolactam melt. After stirring for 0.75 h, volatiles were removed. Yield: 2.39 g (92.6%). The product was dissolved in dichloromethane, filtered, and volatiles were removed. 1H NMR (500 MHz, d6-DMSO): 1.46-1.63 (m, 8H), 2.27 (s, 3H), 2.38 (t, 2H), 3.11 (t, 2H), 7.16 (d, 2H), 7.55 (d, 2H), 8.24 (broad s). 13C NMR (125 MHz, d6-DMSO): 21.21, 22.95, 29.17, 30.08, 35.46, 42.28, 55.28, 125.91, 128.87, 139.32, 144.25, 179.44.

Workup

  1. stirringAfter stirring for 0.75 h
  2. customvolatiles were removed
  3. dissolutionThe product was dissolved in dichloromethane
  4. filtrationfiltered
  5. customvolatiles were removed

Sources & evidence

ORD record
ord-69296767071c4283b2c2b95cd4908513
Source dataset
uspto-grants-2016_01
Patent number
US09233928B2

Reaction notes

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