tert-Butanol → HCID 54443561, compound

HRID 618282Notes

Reaction equation

HRID 618282 reaction equation
[CH3:1][C:2]1[CH:3]=C([CH:7]=[CH:8][CH:9]=1)C=C.[CH3:10][C:11]([OH:14])(C)[CH3:12].C(OCC)(=[O:17])C>O>[CH3:1][C:2]1[CH:3]=[C:10]([C@H:11]([OH:14])[CH2:12][OH:17])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 75291-Ethenyl-3-methylbenzeneHCID 8857Ethyl Acetate

Product 1

HCID 54443561HCID 54443561, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-methylstyrene (1.69 ml, 12.7 mmol), and AD-mix-60 (17.78 g, 12.7 mmol) in water (65 ml) and t-BuOH (65 ml) was stirred at 0° C. for 3.5 h. To this reaction mixture was added Na2SO1 (20 g) and the mixture was stirred at rt for 1 h. The reaction mixture was extractecl with ethyl acetate. The extract was washed with brine, dried (Na2SO4), and concentrated to give 2.07 g of light brown oil, which was purified by column chromatography (silica gel: 110 g, ethyl acetate/hexane:3/2) to afford 1.89 g(98%) of desired product as light brown oil.

Workup

  1. additionTo this reaction mixture was added Na2SO1 (20 g)
  2. washThe extract was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d3a7e5836dc24a70992722f75b27d5da
Source dataset
uspto-grants-1999_09
Patent number
US05952369

Reaction notes

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