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

HRID 1435750Notes

Reaction equation

HRID 1435750 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-2069d35b2c8048c7bf09f378e5da6376
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

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