tert-Butanol → 1-(2-Chlorophenyl)ethane-1,2-diol

HRID 844001Notes

Reaction equation

HRID 844001 reaction equation
[C:1]([OH:5])(C)([CH3:3])[CH3:2].[Cl:6][C:7]1C=[CH:11][CH:10]=[CH:9][C:8]=1C=C.S([O-])([O-])=[O:16].[Na+].[Na+]>O>[Cl:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[CH:1]([OH:5])[CH2:3][OH:16]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 149062-ChlorostyreneHCID 24437Sodium Sulfite

Product 1

HCID 1010261-(2-Chlorophenyl)ethane-1,2-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a vigrouosly stirred mixture of AD-mix (1.4 g) in water (5 ml) and t-butanol (5 ml) at 0° C. was added 1-Chloro-2-vinyl-benzene (0.140 grams, 1.0 mmole) and stirred at 0° C. for 2 hours. To the mixture sodium sulfite (1.5 g) was added and allowed to warm to room temperature for 1 hour. The mixture was extracted with methylene chloride. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated to give a colorless oil (0.190 g). MW 172.61; MS (m/e) 190 (M++18).

Workup

  1. temperatureto warm to room temperature for 1 hour
  2. extractionThe mixture was extracted with methylene chloride
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a883bca043ab46d0aff77ff408483a7b
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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