Sodium Hydroxide → 1-(3-Chlorophenyl)-1,2-ethanediol

HRID 2177053Notes

Reaction equation

HRID 2177053 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH2:9])[CH:3]=1.[Mn]([O-])(=O)(=O)=[O:11].[K+].[OH-:16].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:11])[CH2:9][OH:16])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14905m-ChlorostyreneHCID 516875Potassium Permanganate

Product 1

HCID 153566481-(3-Chlorophenyl)-1,2-ethanediol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 1-chloro-3-vinyl-benzene (1.0 g, 7.2 mmol) and potassium permanganate (1.14 g, 7.2 mmol) in methanol was added 1N sodium hydroxide. The reaction mixture was stirred at room temperature for 1.5 hours. Filtered, extracted with dichloromethane, washed with sodium bicarbonate, brine, dried. Purification by silica gel chromatography (5% methanol in dichloromethane) yielded 250.0 mg of 1-(3-chlorophenyl)ethane-1,2-diol.

Workup

  1. filtrationFiltered
  2. extractionextracted with dichloromethane
  3. washwashed with sodium bicarbonate, brine
  4. customdried
  5. customPurification by silica gel chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-bd15a25ea6d4411fb868c34d8723ddfc
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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