Potassium Carbonate → HCID 10192903, compound

HRID 384805Notes

Reaction equation

HRID 384805 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].Br[CH2:15][CH2:16][CH2:17][CH2:18][Cl:19].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:19][CH2:18][CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19844Methyl VanillateHCID 813641-Bromo-4-chlorobutane

Product 1

HCID 10192903HCID 10192903, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
82.5 °C

Procedure

In a 100 mL volume glass flask equipped with a stirrer, a thermometer and a reflux condenser were placed 10.2 g (54.9 mmol) of methyl 4-hydroxy-3-methoxybenzoate (purity: 98 wt. %), 12.5 g (71.4 mmol) of 4-bromo-1-chlorobutane, 8.3 g (60.4 mmol) of potassium carbonate (purity: 98 wt. %), and 300 mL of acetonitrile. The resulting mixture was refluxed under stirring at 80-85° C. for 8 hours in an argon gas atmosphere. After the reaction was complete, the reaction mixture was filtered and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (gel: Wako gel C-200, eluent: n-hexane), to give 13.6 g (isolated yield: 90.0%, purity: 99% in terms of area percentage by high performance liquid chromatography) of methyl 4-(4-chlorobutoxy)-3-methoxybenzoate as a colorless liquid.

Workup

  1. customIn a 100 mL volume glass flask equipped with a stirrer
  2. temperatureThe resulting mixture was refluxed
  3. filtrationthe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by silica gel column chromatography (gel: Wako gel C-200, eluent: n-hexane)

Sources & evidence

ORD record
ord-b510787083d346078cfec79630216503
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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