4-(1-Methylethyl)benzaldehyde oxime → N-Hydroxy-4-(propan-2-yl)benzene-1-carboximidoyl chloride

HRID 1576986Notes

Reaction equation

HRID 1576986 reaction equation
[Cl:1]OC(C)(C)C.[CH:7]([C:10]1[CH:18]=[CH:17][C:13]([CH:14]=[N:15][OH:16])=[CH:12][CH:11]=1)([CH3:9])[CH3:8]>C(Cl)(Cl)(Cl)Cl>[CH:7]([C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:1])=[N:15][OH:16])=[CH:12][CH:11]=1)([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 963584-(1-Methylethyl)benzaldehyde oximeHCID 521297Tert-Butyl hypochlorite

Product 1

HCID 71391085N-Hydroxy-4-(propan-2-yl)benzene-1-carboximidoyl chlorideYield 72.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 5.4 g of tert-butyl hypochlorite in 25 ml of carbon tetrachloride was added dropwise during 15 minutes into a solution of 6.8 g of 4-isopropylbenzaldoxime (m.p. 61°-63°, prepared in the manner described in Example II) in 50 ml of carbon tetrachloride while the temperature was maintained at 15°-23°. The green mixture was stirred for 15 minutes, then concentrated. The oil was crystallized from hexane to give 6 g of 4-isopropylbenzohydroximoyl chloride.

Workup

  1. customprepared in the manner
  2. temperaturewas maintained at 15°-23°
  3. concentrationconcentrated
  4. customThe oil was crystallized from hexane

Sources & evidence

ORD record
ord-3115642995394c2f80c5d04f8a70cac5
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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