Cornforth reagent → 1-(2,4-Dichlorophenyl)-3-(1,3-dioxan-2-yl)propan-1-one

HRID 462887Notes

Reaction equation

HRID 462887 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])[CH2:3][CH2:4][CH:5]1[O:10][CH2:9][CH2:8][CH2:7][O:6]1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O.O>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:2]([CH2:3][CH2:4][CH:5]1[O:6][CH2:7][CH2:8][CH2:9][O:10]1)=[O:1]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 20281485HCID 20281485, compound

Product 1

HCID 202814991-(2,4-Dichlorophenyl)-3-(1,3-dioxan-2-yl)propan-1-oneYield 93.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[3-hydroxy-3-(2,4-dichlorophenyl)prop-1-yl]-1,3-dioxane (2.91 g) and pyridinium dichromate (6.96 g) in dry dimethylformamide (DMF: 20 ml) was stirred at room temperature for 7 hours. The reaction mixture was diluted with water (100 ml) and extracted with diethyl ether. The extracts were washed with water, dried over magnesium sulphate, and concentrated under reduced pressure to give 2-[2-(2,4-dichlorobenzoyl)ethyl]-1,3-dioxane (2.7 g, 93%) as an orange oil, IR (film): 1700 cm-1.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extracts were washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-471f2182d298489198772a065165b6fc
Source dataset
uspto-grants-1985_05
Patent number
US04518415

Reaction notes

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