Ammonium Chloride → (5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 641847Notes

Reaction equation

HRID 641847 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:22]([O-:24])=[O:23])=[C:9]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[OH:12])[CH:10]=1)[CH:2]=[CH2:3].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(O)[O-].[Na+].[Cl-].[NH4+]>CC(C)=O.C(O)(C)C>[CH2:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:22]([O-:24])=[O:23])=[C:9]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([CH:19]([CH3:20])[CH3:21])=[CH:17][CH:18]=2)=[O:12])[CH:10]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 23665763Sodium BisulfiteHCID 59259038(5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanolHCID 131709961Jones' reagent

Product 1

HCID 59259161(5-Allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 16.38 g (50 mmol) (5-allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanol in 60 ml acetone is treated at 0° C. with 20 ml (53.4 mmol) Jones reagent. After stirring for 2 h at r.t. isopropanol, an aqueous solution of sodium bisulphite and saturated aqueous ammonium chloride solution are added. Extraction with dichloromethane affords (5-allyloxy-2-nitro-phenyl)-(4-isopropyl-phenyl)-methanone.

Workup

  1. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-03e93b81e63e4013a399e0a889ea7a7f
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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