Methanol → Methyl 4-Morpholinobenzoate

HRID 2104437Notes

Reaction equation

HRID 2104437 reaction equation
S(Cl)(Cl)=O.[O:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[CH3:20]O>>[CH3:20][O:16][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:7][CH2:6][O:5][CH2:10][CH2:9]2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 3452784-(Morpholin-4-yl)benzoic acid

Product 1

HCID 5178200Methyl 4-Morpholinobenzoate

Procedure

Under ice cooling, thionyl chloride (436 μL) was added dropwise to methanol (10 mL). 4-Morpholinobenzoic acid (207 mg) was added thereto, and the resultant mixture was heated under reflux for 1.5 hours. The solvent was distilled away under reduced pressure. Methylene chloride and water were added to the residue for partitioning the mixture. The organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, whereby the title compound was obtained.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. distillationThe solvent was distilled away under reduced pressure
  3. additionMethylene chloride and water were added to the residue
  4. customfor partitioning the mixture
  5. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  6. distillationThe solvent was distilled away under reduced pressure, whereby the title compound
  7. customwas obtained

Sources & evidence

ORD record
ord-a09d0fa840a24c5198418cb9e47cc2f8
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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