Dimethylformamide → Methyl 4-(3-chloropropoxy)benzoate

HRID 657608Notes

Reaction equation

HRID 657608 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][Cl:11].CN(C)C=O.[OH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>>[Cl:11][CH2:10][CH2:9][CH2:8][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate

Product 1

HCID 12389265Methyl 4-(3-chloropropoxy)benzoateYield 93.7%

Procedure

A suspension of potassium carbonate (48.4 g) in a mixture of methyl 4-hydroxybenzoate (10.65 g), 1-bromo-3-chloropropane (55.1 g) and N,N-dimethylformamide (100 mL) is stirred at room temperature for 15 h. Solids are separated by filtration and washed three times with ethanol (30 mL). The combined filtrates are concentrated under reduced pressure, and then dissolved in ethyl acetate (200 mL). The organic layer is washed twice with water (50 mL), dried over magnesium sulphate and concentrated under reduced pressure to give 15 g of methyl 4-(3-chloropropoxy)benzoate used without further purification.

Workup

  1. customSolids are separated by filtration
  2. washwashed three times with ethanol (30 mL)
  3. concentrationThe combined filtrates are concentrated under reduced pressure
  4. dissolutiondissolved in ethyl acetate (200 mL)
  5. washThe organic layer is washed twice with water (50 mL)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cdc425459fd84c16addff9e25dfbc454
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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