hydroxylamine-O-sulfonic acid → 3,5-Dioxo-4-palmitoylcyclohexanecarbonitrile

HRID 1614015Notes

Reaction equation

HRID 1614015 reaction equation
[CH:1]([CH:3]1[CH2:8][C:7](=[O:9])[CH:6]([C:10](=[O:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:5](=[O:27])[CH2:4]1)=O.[NH2:28]OS(O)(=O)=O>O>[O:27]=[C:5]1[CH:6]([C:10](=[O:26])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:7](=[O:9])[CH2:8][CH:3]([C:1]#[N:28])[CH2:4]1

Participants

4

Reactant 2

HCID 76284hydroxylamine-O-sulfonic acidHCID 150035705-Formyl-2-palmitoylcyclohexane-1,3-dione

Product 1

HCID 197746893,5-Dioxo-4-palmitoylcyclohexanecarbonitrileYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

43 g (0.12 mol) of 5-formyl-2-palmitoylcyclohexane-1,3-dione were suspended in 150 ml of distilled water. To this were added 15.7 g (0.14 mol) of hydroxylamine-O-sulfonic acid dissolved in 50 ml of water. The heterogeneous reaction mixture was stirred at room temperature overnight. The resulting solid was filtered off with suction, washed with water and dried. 37.7 g (86% of theory) of 3,5-dioxo-4-palmitoylcyclohexanecarbonitrile were isolated (melting point 66° to 69° C).

Workup

  1. filtrationThe resulting solid was filtered off with suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-e8ec7719ba694eecb6e1a574018214d5
Source dataset
uspto-grants-1993_03
Patent number
US05194650

Reaction notes

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