Potassium Carbonate → Methyl 3-(2-morpholin-4-ylethoxy)benzoate

HRID 1278859Notes

Reaction equation

HRID 1278859 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:16]1([CH2:15][CH2:14][O:1][C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 7164628Methyl 3-(2-morpholin-4-ylethoxy)benzoateYield 60.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-hydroxybenzoate (8.0 g, 56 mmol) and 4-(2-chloroethyl)-morpholine hydrochloride (15.7 g, 84 mmol) and potassium carbonate (11.5 g, 83 mmol) in toluene (50 ml) was heated at reflux. After 4 days, the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water and then extracted with dilute hydrochloric acid. The acidic layer was separated, basified with 5 N sodium hydroxide and the product was extracted into ethyl acetate. The organics were removed in vacuo and the residue was purified by flash chromatography (elution gradient 3% acetone/methylene chloride) to give methyl 3-(2-morpholin-4-ylethoxy)benzoate (9.0 g) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. washThe organic layer was washed with water
  4. extractionextracted with dilute hydrochloric acid
  5. customThe acidic layer was separated
  6. extractionthe product was extracted into ethyl acetate
  7. customThe organics were removed in vacuo
  8. customthe residue was purified by flash chromatography (elution gradient 3% acetone/methylene chloride)

Sources & evidence

ORD record
ord-5491e9890287446e8f8320a8987709cf
Source dataset
uspto-grants-2002_09
Patent number
US06444696B1

Reaction notes

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