Potassium Carbonate → HCID 21958890, compound

HRID 2233236Notes

Reaction equation

HRID 2233236 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[C:11]([O:22][CH2:23][CH3:24])(=[O:21])[C:12]1[CH:20]=[CH:19][C:17]([OH:18])=[C:14]([O:15][CH3:16])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:16][O:15][C:14]1[CH:13]=[C:12]([CH:20]=[CH:19][C:17]=1[O:18][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[C:11]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12038Ethyl vanillateHCID 958344-(3-Chloropropyl)morpholine

Product 1

HCID 21958890HCID 21958890, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-(3-Chloropropyl)morpholine (90 g, 0.55 mol) was added dropwise, over 30 minutes, to a solution of ethyl vanillate (98 g, 0.50 mol) and powdered potassium carbonate (104 g, 0.75 mol) in dimethylformamide (300 ml) at 80° C. The reaction was heated at 80° C. for 90 minutes, cooled to ambient temperature, filtered and the filtrate concentrated in vacuo. The crude product was taken up in diethyl ether (1000 ml), filtered and washed with water (2×200 ml) and brine (200 ml). Solvent evaporation in vacuo yielded ethyl 3-methoxy-4-(3-morpholinopropoxy)benzoate (161.5 g, 100% yield) as a pale yellow oil which crystallised on standing to afford a pale yellow solid:

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vacuo
  4. filtrationfiltered
  5. washwashed with water (2×200 ml) and brine (200 ml)
  6. customSolvent evaporation in vacuo

Sources & evidence

ORD record
ord-6e3a4dcc0922484e9975e4ad70090ddd
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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