Ethanol → 4-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acid

HRID 1795576Notes

Reaction equation

HRID 1795576 reaction equation
C([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([CH3:18])[CH:11]=1)([CH3:9])[CH3:8])C.C(O)C.[OH-].[K+]>O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]([CH3:8])([CH3:9])[CH2:6][CH2:5][C:4]([OH:19])=[O:3])=[CH:11][C:12]=1[CH3:18]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21024370HCID 21024370, compound2×

Product 1

HCID 222183274-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(4-methoxy-3-methylphenyl)-4-methyl-pentanoic acid ethyl ester (Compound 4, 6.8 g, 25.8 mmol) and 20 mL of absolute ethyl alcohol was added aqueous 5 M KOH (6 mL). The resulting solution was heated in an 60° C. bath for 24 h. The solution was cooled to room temperature, diluted with water and washed once with 2:1 hexane:ethyl acetate solution, and the layers were separated. The aqueous layer was acidified with HCl 2 N to pH=0-1 and the product extracted three times with ethyl acetate. The combined organic extracts were washed with brine, and dried over MgSO4, and filtered. The solvent was removed to give 5.9 g (97%) of the title compound as a dark oil.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washwashed once with 2:1 hexane
  3. customethyl acetate solution, and the layers were separated
  4. extractionthe product extracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-45a67a93d7b145e98af080014b58e6fb
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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