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

HRID 1364475Notes

Reaction equation

HRID 1364475 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-a8366b1f4b2d4dc299ebd1f68953c079
Source dataset
uspto-grants-2011_02
Patent number
US07888366B2

Reaction notes

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