Hydrochloric Acid → HCID 17816475, compound

HRID 2249682Notes

Reaction equation

HRID 2249682 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[C:11]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:10]=1)[C:2]1C=CC=CC=1.[H][H].Cl.C(Cl)(=[O:29])C>C(OCC)(=O)C.C(O)C.[C].[Pd].O.C(N(CC)CC)C.C(Cl)(Cl)Cl>[C:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:10]=1)(=[O:29])[CH3:2]

Participants

11

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6367Acetyl chlorideHCID 10757637HCID 10757637, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 17816475HCID 17816475, compound

Reagents, catalysts & solvents 6

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
50 °C

Procedure

In a mixture of 15 ml of ethyl acetate and 15 ml of ethanol is dissolved 5.00 g of methyl 4-(benzyloxy)-2-isobutoxybenzoate, to which is added 1.0 g of 5% palladium-carbon. The mixture thus obtained is stirred at ambient temperature for 3 hours in a stream of hydrogen. The reaction mixture is filtered with Celite, and the solvent is distilled off therefrom under reduced pressure. Then, 19 ml of 5 mol/L solution of sodium hydroxide is added to a solution of the residue obtained above in 35 ml of ethanol, and the mixture thus obtained is stirred at 50° C. for one hour. The reaction mixture is added to a mixture of chloroform and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. To a solution of the residue thus obtained in 20 ml of tetrahydrofuran are successively added 2.0 ml of triethylamine and 0.8 ml of acetyl chloride, and the mixture thus obtained is stirred at ambient temperature for 10 minutes. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer 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. Thus, 1.37 g of 4-acetyloxy-2-isobutoxybenzoic acid is obtained as a light yellow oily product.

Workup

  1. customThe mixture thus obtained
  2. filtrationThe reaction mixture is filtered with Celite
  3. distillationthe solvent is distilled off
  4. additionThen, 19 ml of 5 mol/L solution of sodium hydroxide is added to a solution of the residue
  5. customobtained above in 35 ml of ethanol
  6. customthe mixture thus obtained
  7. customthe organic layer is separated
  8. customTo a solution of the residue thus obtained in 20 ml of tetrahydrofuran
  9. customthe mixture thus obtained
  10. stirringis stirred at ambient temperature for 10 minutes
  11. customthe organic layer is separated
  12. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  13. dry with materialdried over anhydrous magnesium sulfate
  14. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-e084f115b48546a2bb2327d55e7f55ec
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

Loading…