Potassium Carbonate → 5-(4-Methoxy-2,5-dimethylphenoxy)-2,2-dimethyl-pentanoic acid, methyl ester

HRID 374284Notes

Reaction equation

HRID 374284 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:11])[C:6]([OH:10])=[CH:7][C:8]=1[CH3:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24]>C(#N)C>[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([O:10][CH2:19][CH2:20][CH2:21][C:22]([CH3:28])([CH3:27])[C:23]([O:25][CH3:26])=[O:24])=[C:5]([CH3:11])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 13050502Methyl 5-bromo-2,2-dimethylpentanoateHCID 137511404-Methoxy-2,5-dimethylphenol

Product 1

HCID 867463855-(4-Methoxy-2,5-dimethylphenoxy)-2,2-dimethyl-pentanoic acid, methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 500 mL, 3 neck round bottom flask is charged with 7.6 g (50 mmol) of 4-methoxy-2,5-xylenol, 8.3 g (60 mmol) of anhydrous potassium carbonate 13.4 g (60 mmol) of 5-bromo-2,2-dimethylvaleric acid, methyl ester (U.S. Pat. No. 4,665,226) and 150 mL of acetonitrile. The mixture is stirred mechanically at reflux for 24 hours. The reaction flask and inorganic solids are washed with fresh acetonitrile and the filtrate evaporated. The residue is taken up in diethyl ether and the solution washed with 50 mL of 2N potassium hydroxide solution, brine, dried (magnesium sulfate) and evaporated. The crude product amounts to 16.6 g. Distillation through a short path apparatus first at aspirator pressure and then at 0.5 mm affords 12.9 g of the title compound; infrared spectrum (IR) (C=0) 1732 cm-1.

Workup

  1. temperatureat reflux for 24 hours
  2. washThe reaction flask and inorganic solids are washed with fresh acetonitrile
  3. customthe filtrate evaporated
  4. washthe solution washed with 50 mL of 2N potassium hydroxide solution, brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. distillationDistillation through a short path apparatus first at aspirator pressure

Sources & evidence

ORD record
ord-caf57d8f8dd14906a03aa79932c753d1
Source dataset
uspto-grants-1992_11
Patent number
US05166398

Reaction notes

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