Acetonitrile → HCID 69015832, compound

HRID 1591624Notes

Reaction equation

HRID 1591624 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].Br[CH2:19][CH2:20][O:21][CH3:22].[C:23](#N)[CH3:24]>>[CH3:22][O:21][CH2:20][CH2:19][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:23][CH2:24][O:15][CH3:12]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 94475-Chlorosalicylic AcidHCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 69015832HCID 69015832, compoundYield 93%

Procedure

A mixture of 5-chlorosalicylic acid (5.0 g, 29.0 mmol), potassium carbonate (10.8 g, 78.1 mmol), acetonitrile (100 ml), and 2-bromoethylmethyl ether (6.8 ml, 72.3 mmol) was heated under reflux for 20 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (50 ml). The solution was washed with aqueous sodium hydroxide solution (1 M, 2×50 ml), washed with water (50 ml), dried over sodium sulfate, and concentrated under reduced pressure to provide 5-chloro-2-(2-methoxyethoxy)benzoic acid 2-methoxyethyl ester (7.83 g, 93% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 hours
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  6. washThe solution was washed with aqueous sodium hydroxide solution (1 M, 2×50 ml)
  7. washwashed with water (50 ml)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69b0a7e836f843c4b9be76af1f187a73
Source dataset
uspto-grants-2007_11
Patent number
US07291616B2

Reaction notes

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