Lithium hydroxide, monohydrate → 4-(Morpholinomethyl)phenol

HRID 2097368Notes

Reaction equation

HRID 2097368 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)(=O)C.O[Li].O>CO.O>[O:15]1[CH2:14][CH2:13][N:12]([CH2:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 231324404-(Morpholinomethyl)phenyl acetate

Product 1

HCID 7833224-(Morpholinomethyl)phenol

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 4-(morpholinomethyl)phenyl acetate (1.9 g, 8.1 mmol) in 1:1 methanol/water (40 mL) at 0° C. was added LiOH.H2O (339 mg, 8.1 mmol). The reaction was stirred at RT for 2 h. The mixture was concentrated to remove methanol, and the aqueous layer acidified with 3 N HCl. The aqueous layer was extracted with ethyl acetate (4×30 mL) and the organics dried and concentrated to give 454 mg recovered starting material. The aqueous layer was then made basic again (to pH 9) with 1 N NaOH and extracted with ethyl acetate (7×20 mL). These combined organics were washed with brine, dried with Na2SO4, and concentrated to give a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove methanol
  3. extractionThe aqueous layer was extracted with ethyl acetate (4×30 mL)
  4. customthe organics dried
  5. concentrationconcentrated
  6. customto give 454 mg
  7. customrecovered
  8. extractionextracted with ethyl acetate (7×20 mL)
  9. washThese combined organics were washed with brine
  10. dry with materialdried with Na2SO4
  11. concentrationconcentrated
  12. customto give a white solid

Sources & evidence

ORD record
ord-9b9d2484977242fab73e6385fda9f107
Source dataset
uspto-grants-2013_05
Patent number
US08450348B2

Reaction notes

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