Hydrochloric Acid → Methyl 2-(2-isobutoxyphenyl)acetate

HRID 2249667Notes

Reaction equation

HRID 2249667 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](O)=O)[CH:2]([CH3:4])[CH3:3].S(Cl)(Cl)=O.[N+](=C)=[N-].CN(N=O)[C:24](N)=[O:25].[OH-].[K+].Cl.[CH2:32]([O:34]CC)C>C(Cl)Cl.CO.C([O-])(=O)C1C=CC=CC=1.[Ag+].O.C(OCC)(=O)C.C(N(CC)CC)C.C(O)(=O)C>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[CH2:8][C:32]([O:25][CH3:24])=[O:34])[CH:2]([CH3:4])[CH3:3]

Participants

15

Reactant 7

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether3×HCID 9550DiazomethaneHCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 24386Thionyl ChlorideHCID 149555242-(2-Methylpropoxy)benzoic acid

Product 1

HCID 17816558Methyl 2-(2-isobutoxyphenyl)acetate

Reagents, catalysts & solvents 7

HCID 164649Silver benzoateCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent3×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 40 ml of methylene chloride are dissolved 3.8 g of 2-isobutoxybenzoic acid and 2.8 ml of thionyl chloride. The solution is heated under reflux for one hour with stirring. The reaction mixture obtained herein is dropwise added at 5-10° C. to a solution of diazomethane in ethyl ether prepared from 53.0 g of N-methylnitrosourea, 83.0 g of potassium hydroxide, 120 ml of water and 150 ml of ethyl ether, and the mixture thus obtained is stirred at ambient temperature for 2 hours. Ethyl ether, acetic acid and water are added to the reaction mixture, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is dissolved in 30 ml of methanol, and the resulting solution is added to a mixture of 2.3 g of silver benzoate and 23 ml of triethylamine at 25-30° C., and stirred for 1.5 hours. Ethyl acetate and water are added to the reaction mixture, pH is adjusted to 2.0 with concentrated hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to obtain 3.8 g of methyl 2-(2-isobutoxyphenyl)acetate as a colorless oily product.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for one hour
  3. customThe reaction mixture obtained herein
  4. customthe mixture thus obtained
  5. stirringis stirred at ambient temperature for 2 hours
  6. customthe organic layer is separated
  7. customThe organic layer thus obtained
  8. washis washed with water and saturated aqueous solution of sodium chloride successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. customThe residue thus obtained
  12. stirringstirred for 1.5 hours
  13. customthe organic layer is separated
  14. customThe organic layer thus obtained
  15. washis washed with water and saturated aqueous solution of sodium chloride successively
  16. dry with materialdried over anhydrous magnesium sulfate
  17. distillationthe solvent is distilled off under reduced pressure
  18. customThe residue is purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-bfd0879035be4c78afc471b6d3d11d8e
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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