2-Methyl-2-butene → HCID 67236283, compound

HRID 1026785Notes

Reaction equation

HRID 1026785 reaction equation
[C:1]([O:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=[O:10])(=[O:3])[CH3:2].CC(=CC)C.P([O-])([O-])(O)=[O:21].[Na+].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:1]([O:4][CH2:5][O:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]([OH:21])=[O:10])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 24203Sodium Phosphate, DibasicHCID 23668197Sodium ChloriteHCID 54127100HCID 54127100, compound

Product 1

HCID 67236283HCID 67236283, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

21.79 g (112.2 mmol) of 2-acetoxymethoxy-benzaldehyde and 100 ml (900 mmol) of 2-methyl-2-butene are diluted in 400 ml of tert-butanol. A solution containing 41 g (337 mmol) of sodium hydrogen phosphate and 35 g (393 mmol) of sodium chlorite in 100 ml of water is added dropwise to the reaction mixture, which is stirred for 2 hours at room temperature. The mixture is evaporated under reduced pressure and the residue is dissolved in dichloromethane. The organic phase is washed with water, dried over magnesium sulphate, filtered and concentrated. The white solid obtained is precipitated in heptane at 0° C. The precipitate is filtered, then rinsed with heptane and dried. 14.8 g of 2-acetoxymethoxy-benzoic acid is obtained in the form of white powder at a yield of 63%.

Workup

  1. additionis added dropwise to the reaction mixture, which
  2. customThe mixture is evaporated under reduced pressure
  3. dissolutionthe residue is dissolved in dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe white solid obtained
  9. customis precipitated in heptane at 0° C
  10. filtrationThe precipitate is filtered
  11. washrinsed with heptane
  12. customdried

Sources & evidence

ORD record
ord-0d807e237c5249d98d9ddae03caa8bc3
Source dataset
uspto-grants-2014_05
Patent number
US08729312B2

Reaction notes

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