Potassium Carbonate → HCID 22261544, compound

HRID 1610737Notes

Reaction equation

HRID 1610737 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[C:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O.C(OCC)(=O)C.O.[Cl-].[Na+].O>[CH2:18]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 22261544HCID 22261544, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of methyl 3-hydroxybenzoate (7.68 g, 50.5 mmol) in N,N-dimethylformamide (100 ml) were added potassium carbonate (13.96 g, 101 mmol) and neopentyl iodide (10 g, 50.5 mmol), and the mixture was stirred at 100° C. overnight. The mixture was diluted with ethyl acetate, water and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1, 10:1) to give methyl 3-(neopentyloxy)benzoate (4.69 g, 42%) as a colorless transparent oil.

Workup

  1. dry with materialdried over anhydrous magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1, 10:1)

Sources & evidence

ORD record
ord-8829ff91783c4eefa1c5147a5bbc2d2c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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