Ethyl Salicylate → HCID 410450, compound

HRID 619172Notes

Reaction equation

HRID 619172 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CN(C=O)C>[N:24]1([CH2:23][CH2:22][CH2:21][O:1][C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8365Ethyl SalicylateHCID 11430Potassium CarbonateHCID 122962834-(3-Chloropropyl)morpholinium chloride

Product 1

HCID 410450HCID 410450, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of ethyl 2-hydroxybenzoate (2.4 ml, 16.38 mmol), K2CO3 (4.98 g), and DMF (30 ml) was added N-(3-chloropropyl)morpholine hydrochloride (3.93 g). The mixture was stirred at room temperature for 30 minutes, then was warmed on a steam bath overnight. The reaction mixture was cooled, filtered and stripped to afford a liquid which was partitioned between EtOAc (350 ml) and water. The organic layer was separated, washed with water (2×200 ml), dried over MgSO4 and stripped to afford ethyl 2-[3-(4-morpholinyl)propoxy]benzoate.

Workup

  1. temperaturewas warmed on a steam bath overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto afford a liquid which
  5. customwas partitioned between EtOAc (350 ml) and water
  6. customThe organic layer was separated
  7. washwashed with water (2×200 ml)
  8. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-5c1f5bf9fd6d43d98bca00ad7a9d7017
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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