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

HRID 384781Notes

Reaction equation

HRID 384781 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-].[Na+]>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 5234Sodium ChlorideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 19844Methyl Vanillate

Product 1

HCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoateYield 99.5%

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 (17.5 mmol) of sodium chloride, and 10 mL of acetone. The resulting mixture was refluxed under stirring at 55-60° C. in an argon gas atmosphere for 5 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 1.41 g (reaction yield: 99.5%) 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-91fadcc3ffa944e88ee0b4a24e1e7870
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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