2-Methyl-2-butene → 2-(Tert-butoxycarbonyloxy)benzoic acid

HRID 511917Notes

Reaction equation

HRID 511917 reaction equation
[C:1]([O:5][C:6]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(=CC)C.P([O-])([O-])(O)=[O:23].[Na+].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:1]([O:5][C:6]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]([OH:23])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 24203Sodium Phosphate, DibasicHCID 17748171Carbonic acid tert-butyl ester 2-formyl-phenyl esterHCID 23668197Sodium Chlorite

Product 1

HCID 672090582-(Tert-butoxycarbonyloxy)benzoic acidYield 70.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

21.5 g (93.8 mmol) of 2-(tert-butoxycarbonyloxy)-benzaldehyde and 80 ml (750 mmol) of 2-methyl-2-butene are diluted in 250 ml of tert-butanol. A solution containing 28.1 g (234 mmol) of sodium hydrogenphosphate and 29.7 g (328 mmol) of sodium chlorite in 75 ml of water is added dropwise to the reaction medium, which is stirred at ambient temperature for 2 hours. 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 from heptane at 0° C. The precipitate is filtered off and then rinsed with heptane and dried. 15.8 g of 2-(tert-butoxycarbonyloxy)benzoic acid are obtained in the form of a white powder with a yield of 70%.

Workup

  1. additionis added dropwise to the reaction medium, 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 from heptane at 0° C
  10. filtrationThe precipitate is filtered off
  11. washrinsed with heptane
  12. customdried

Sources & evidence

ORD record
ord-c5010a7e6cfd4cab91bf307ca4108741
Source dataset
uspto-grants-2015_08
Patent number
US09102607B2

Reaction notes

Loading…