Hydroxyamine hydrochloride → HCID 86644089, compound

HRID 2361569Notes

Reaction equation

HRID 2361569 reaction equation
[CH3:1][C:2]1[CH2:7][CH2:6][C:5]([CH:10]=[CH2:11])([CH:8]=O)[CH2:4][CH:3]=1.[CH3:12][C:13]1[CH2:14][C:15]([CH:21]=[CH2:22])([CH:19]=O)[CH2:16][CH2:17][CH:18]=1.Cl.[NH2:24][OH:25].C([O-])(O)=O.[Na+]>CCO.O.O>[CH3:1][C:2]1[CH2:7][CH2:6][C:5]([CH:10]=[CH2:11])([CH:8]=[N:24][OH:25])[CH2:4][CH:3]=1.[CH3:12][C:13]1[CH2:14][C:15]([CH:21]=[CH2:22])([CH:19]=[N:24][OH:25])[CH2:16][CH2:17][CH:18]=1

Participants

8

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59440843HCID 59440843, compoundHCID 59440846HCID 59440846, compound

Product 2

HCID 86644089HCID 86644089, compoundHCID 86644090HCID 86644090, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution of a mixture of 4-methyl-1-vinyl-cyclohex-3-enecarbaldehyde and 3-methyl-1-vinyl-cyclohex-3-ene-carbaldehyde (6:4, 1.5 g, 10 mmol), hydroxylamine hydrochloride (1.04 g, 15 mmol) and NaHCO3 (1.26 g, 15 mmol) in EtOH/Water (20 ml, 3:1) was stirred at 50° C. for 4 h. The mixture was diluted with water and extracted 3 times with MTBE. The combined org. layers were washed with water and brine, dried (MgSO4) and evaporated in vacuo. 4-Methyl-1-vinyl-cyclohex-3-enecarbaldehyde oxime and 3-methyl-1-vinyl-cyclohex-3-ene-carbaldehyde oxime was obtained after bulb-to-bulb distillation (ratio 6:4, yield 70%) as a colorless oil.

Workup

  1. extractionextracted 3 times with MTBE
  2. washlayers were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b4b9d3ad36d646e7820c8d1e707f5c0e
Source dataset
uspto-grants-2014_04
Patent number
US08691746B2

Reaction notes

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