Potassium Chloride → Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

HRID 384780Notes

Reaction equation

HRID 384780 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][Cl:18].C(=O)([O-])[O-].[K+].[K+].[Cl-].[K+]>CC(C)=O>[Cl: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

6

Reactant 4

HCID 4873Potassium ChlorideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoateYield 98.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
57.5 °C

Procedure

In a 50 mL volume glass flask equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser were placed 1.02 g (5.49 mmol) of methyl 4-hydroxy-3-methoxybenzoate (purity: 98 wt. %), 2.12 g (13.2 mmol) of 3-bromo-1-chloropropane (purity: 98 wt. %), 1.16 g (8.24 mmol) of potassium carbonate (purity: 98 wt. %), 1.02 g (13.7 mmol) of potassium chloride, and 10 mL of acetone. The resulting mixture was refluxed under stirring at 55-60° C. in an argon gas atmosphere for 10 hours. After the reaction was complete, the reaction mixture was filtered. Analysis of the filtrate by high performance liquid chromatography (absolute quantitative analysis) indicated that 1.39 g (reaction yield: 98.2%) of methyl 4-(3-chloropropoxy)-3-methoxybenzoate was produced.

Workup

  1. customIn a 50 mL volume glass flask equipped with a stirrer
  2. temperatureThe resulting mixture was refluxed
  3. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-726736c4108d4e0fadb66fd1c630d6eb
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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