1-Bromopropane → Methyl 5-chloro-2-propoxybenzoate

HRID 1591619Notes

Reaction equation

HRID 1591619 reaction equation
Br[CH2:2][CH2:3][CH3:4].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([OH:16])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([O:16][CH2:2][CH2:3][CH3:4])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Product 1

HCID 69015988Methyl 5-chloro-2-propoxybenzoateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-bromo-propane (1 ml, 11 mmol), methyl 5-chloro-2-hydroxy-benzoate (1.0 g, 5.4 mmol), potassium carbonate (1.5 g, 10.9 mmol), and acetonitrile (20 ml) was heated under reflux for 4 hours. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium chloride solution (50 ml). The organic layer was concentrated under reduced pressure to provide methyl 5-chloro-2-propoxy-benzoate (1.2 g, 97% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was partitioned between ethyl acetate (100 ml) and saturated aqueous sodium chloride solution (50 ml)
  6. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d6e00203d39e42e89b75fe26d329a5e9
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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