Toluene → HCID 23295251, compound

HRID 1955347Notes

Reaction equation

[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.S([O-])([O-])(=O)=O.[OH:16][NH3+:17].O[NH3+].[OH-].[Na+].[C:22]1([CH3:28])C=CC=CC=1>>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]1[CH2:28][CH2:22][O:16][N:17]=1

Participants

Reactant 4

HCID 1140Toluene

HCID 67372,6-Dichlorobenzaldehyde2×

HCID 14798Sodium Hydroxide

HCID 24846Hydroxylamine sulfate

Product 1

HCID 23295251HCID 23295251, compound

Procedure

Starting from 2,6-dichlorobenzaldehyde 75 g (0.43 mol) of 2,6-dichlorobenzaldehyde were dissolved in 400 ml of toluene and then 155 g (0.24 mol) of 25% strength hydroxylammonium sulfate solution were added. At 75° C., 38 g of 50% strength NaOH were added dropwise. After stirring for half an hour, the phases were separated at 75° C., and the organic phase was washed with water and then cooled. At 25° C., 276 g (0.46 mol) of 12.5% strength sodium hypochlorite solution were added dropwise over 4-6 h while simultaneously passing in ethylene. After addition of the hypochlorite solution was complete, the mixture was stirred for 1 h, the phases were separated, the organic phase was washed with water, and the solvent was distilled off under reduced pressure. 82 g (89% of theory) of the required product were obtained with a purity (by GC) of 96%.

Workup

customthe phases were separated at 75° C.
washthe organic phase was washed with water
temperaturecooled
additionAt 25° C., 276 g (0.46 mol) of 12.5% strength sodium hypochlorite solution were added dropwise over 4-6 h
additionAfter addition of the hypochlorite solution
stirringthe mixture was stirred for 1 h
customthe phases were separated
washthe organic phase was washed with water
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-4acb424308c440e781d5dcd2ebf8d50e
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06124469

Reaction notes

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