Water → 1-(4-Tert-butylphenyl)ethane-1,2-diol

HRID 1392884Notes

Reaction equation

HRID 1392884 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].C([CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.S([O-])([O-])=[O:19].[Na+].[Na+].[OH2:24]>>[C:1]([C:15]1[CH:14]=[CH:13][C:12]([CH:11]([OH:19])[CH2:10][OH:24])=[CH:17][CH:16]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 138033tert-Butylstyrene

Product 1

HCID 190777511-(4-Tert-butylphenyl)ethane-1,2-diol

Procedure

To a 100 ml round bottom flask is added 20 ml tert butanol, 20 ml of water and 5.6 g of AD-mix-P. The solution is stirred and cooled to 0° C. tert-butyl styrene (0.64 g, 4 mmol) is added to the mixture and the resulting solution is stirred overnight at 0 C. Solid sodium sulfite (6 g) is added and the mixture stirred for an additional 30 minutes. The solution is then extracted in ethyl acetate, washed with water and dried. The crude is then purified by flash chromatography (silica gel; ethyl acetate/hexanes) to afford the product.

Workup

  1. additionis added to the mixture
  2. stirringthe resulting solution is stirred overnight at 0 C
  3. stirringthe mixture stirred for an additional 30 minutes
  4. extractionThe solution is then extracted in ethyl acetate
  5. washwashed with water
  6. customdried
  7. customThe crude is then purified by flash chromatography (silica gel; ethyl acetate/hexanes)
  8. customto afford the product

Sources & evidence

ORD record
ord-b473e69c76fc45c2bc52fabd7125d26e
Source dataset
uspto-grants-2008_03
Patent number
US07344702B2

Reaction notes

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