1-Bromo-3-chloropropane → Methyl 4-(3-chloropropoxy)-3-methoxybenzoate

HRID 384776Notes

Reaction equation

HRID 384776 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+]>CO>[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

5

Reactant 3

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

Product 1

HCID 14407173Methyl 4-(3-chloropropoxy)-3-methoxybenzoateYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
64.5 °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. %), and 30 mL of methanol. The resulting mixture was under stirring at 62-67° 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 1.23 g (reaction yield: 86.5%) of methyl 4-(3-chloropropoxy)-3-methoxybenzoate was produced.

Workup

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

Sources & evidence

ORD record
ord-b145074ecbad41ea90dcafc97927c688
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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