Citric Acid → 2-(Benzyloxy)-5-(morpholin-4-yl)benzoic acid

HRID 454509Notes

Reaction equation

[OH-].[Na+].C(O)C.[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:15]=1[C:16]([O:18]C)=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C>[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[CH:20][C:15]=1[C:16]([OH:18])=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A 4 mol/L aqueous solution of sodium hydroxide (0.3 mL) was added to an ethanol (2.1 mL) solution of the obtained methyl 2-(benzyloxy)-5-(morpholin-4-yl)benzoate (0.26 g), followed by stirring at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and then a 10% aqueous solution of citric acid and ethyl acetate were sequentially added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the obtained residue, and the solid substance was collected by filtration to obtain 0.17 g of 2-(benzyloxy)-5-(morpholin-4-yl)benzoic acid as a white solid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe organic layer was separated
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
additionDiisopropyl ether was added to the obtained residue
filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record: ord-a5d0d94497434f24a4e53fcaf1aedbdb
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492582B2

Reaction notes

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