(4-Isopropyl-phenyl)-(2-nitro-5-propargyloxy-phenyl)-methanol → (4-Isopropylphenyl)(2-nitro-5-(prop-2-yn-1-yloxy)phenyl)methanone

HRID 641817Notes

Reaction equation

HRID 641817 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[N+:22]([O-:24])=[O:23])[OH:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([C:12]2[CH:17]=[C:16]([O:18][CH2:19][C:20]#[CH:21])[CH:15]=[CH:14][C:13]=2[N+:22]([O-:24])=[O:23])=[O:11])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 59259026(4-Isopropyl-phenyl)-(2-nitro-5-propargyloxy-phenyl)-methanolHCID 131709961Jones' reagent

Product 1

HCID 45480510(4-Isopropylphenyl)(2-nitro-5-(prop-2-yn-1-yloxy)phenyl)methanone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an ice cold solution of (4-isopropyl-phenyl)-(2-nitro-5-propargyloxy-phenyl)-methanol in 200 ml acetone are added dropwise 60 ml Jones reagent. After stirring for 2 h at rt the reaction is quenched by the addition of isopropanol and sodium bisulphite solution (40%). Extraction with dichloromethane affords (4-isopropyl-phenyl)-(2-nitro-5-propargyloxy-phenyl)-methanone.

Workup

  1. customis quenched by the addition of isopropanol and sodium bisulphite solution (40%)
  2. extractionExtraction with dichloromethane

Sources & evidence

ORD record
ord-94217c58e7d5439d9ef40a497f8a84d6
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

Loading…