Hydrochloric Acid → 4-[2-(Morpholin-4-yl)ethoxy]benzoic acid

HRID 252840Notes

Reaction equation

HRID 252840 reaction equation
[OH-].[Li+].[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[CH2:5][CH2:4]1.C1COCC1.O.Cl>CS(C)=O>[O:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][O:11][C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 16111873HCID 16111873, compoundHCID 21881883Oxolane--water (1/1)

Product 1

HCID 65042324-[2-(Morpholin-4-yl)ethoxy]benzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Lithium hydroxide (hydrated) (0.59 g, 14.1 mmol) was added to a solution of methyl 4-(2-morpholinoethoxy)benzoate 193 (1.25 g, 4.7 mmol) in a 1:1 mixture of THF-water (20 mL). The reaction mixture was stirred at rt overnight then acidified with 1N HCl to pH 2, solvent was evaporated and the residue was lyophilized to provide crude 194 (1.66 g, >>100% Yield). 1H NMR: (DMSO) δ (ppm): 400 MHz, (DMSO) d (ppm): 7.88 (d, J=8.8 Hz, 2H), 7.05 (d, J=8.8 Hz, 2H), 4.53 (m, 2H), 3.89 (m, 4H), 3.53 (m, 2H), 3.26 to 3.14 (m, 4H). MS: 251.12 (calc), 252.1 (obs).

Workup

  1. customwas evaporated
  2. customto provide crude 194 (1.66 g, >>100% Yield)

Sources & evidence

ORD record
ord-56fa750b89224b6c8d3a0739cb0241f2
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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