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

HRID 1166639Notes

Reaction equation

HRID 1166639 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 5M 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 2N 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-c0db8e68053d4a929d4422e92a3677d6
Source dataset
uspto-grants-2003_09
Patent number
US06613917B1

Reaction notes

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