4-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acid → HCID 12088903, compound

HRID 1795577Notes

Reaction equation

HRID 1795577 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][C:4]=1[CH3:17]>CS(O)(=O)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6]([C:9]([CH3:16])([CH3:15])[CH2:10][CH2:11][C:12]2=[O:14])=[CH:5][C:4]=1[CH3:17]

Participants

3

Reactant 1

HCID 222183274-Methoxy-gamma,gamma,3-trimethylbenzenebutanoic acid2×

Product 1

HCID 12088903HCID 12088903, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 4-(4-methoxy-3-methylphenyl)-4-methyl-pentanoic acid (Compound 5, 7.8 g, 33 mmol) and 150 mL of methanesulfonic acid was stirred at room temperature under an argon atmosphere for 24 h, then poured into ice, extracted three times with ethyl acetate, washed with NaHCO3 1 N, brine, and dried over MgSO4, and filtered. The solvent was removed, and the residue was purified by flash chromatography (Hexane:Ethyl Acetate=4:1) to afford 3.9 g (54%) of the title compound as a yellow solid.

Workup

  1. additionpoured into ice
  2. extractionextracted three times with ethyl acetate
  3. washwashed with NaHCO3 1 N, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed
  7. customthe residue was purified by flash chromatography (Hexane:Ethyl Acetate=4:1)

Sources & evidence

ORD record
ord-31b880db4c264fd9ba41b3b554158a5c
Source dataset
uspto-grants-2006_04
Patent number
US07026487B2

Reaction notes

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