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

HRID 1533832Notes

Reaction equation

HRID 1533832 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-palmitoylcyclo-hexane-1,3-dione were suspended in 150 ml of distilled water. 15.7 g (0.14 mol) of hydroxylamine-O-sulfonic acid, dissolved in 50 ml of water, were added. The heterogeneous reaction mixture was stirred overnight at room temperature. The solid obtained was filtered off under suction, washed with water and dried. 37.7 g (86% of theory) of 3,5-dioxo-4-palmitoylcyclohexanenitrile of melting point 66-69° C. were isolated.

Workup

  1. additionwere added
  2. customThe solid obtained
  3. filtrationwas filtered off under suction
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-63461baa0b9e4399a1c4ebeac9db652e
Source dataset
uspto-grants-1992_02
Patent number
US05085689

Reaction notes

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