Sodium Hydroxide → 4-[(Oxan-4-yl)oxy]benzoic acid

HRID 2202069Notes

Reaction equation

HRID 2202069 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>CO.O>[O:1]1[CH2:2][CH2:3][CH:4]([O:7][C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57770570HCID 57770570, compound

Product 1

HCID 242295194-[(Oxan-4-yl)oxy]benzoic acidYield 98.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-((tetrahydro-2H-pyran-4-yl)oxy)benzoate (400 mg, 1.6 mmol) in MeOH (10 ml) was added a solution of NaOH (128 mg, 3.2 mmol) in H2O (4 mL) at 22° C. The mixture was stirred at 50° C. for 4 h. The mixture was concentrated and the residue was treated with water and extracted with EA. The water layer was treated with 2N HCl to pH=3. The water layer was then extracted with EA. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give the title product which was used in next step without further purification (350 mg, Yield 98.6%). 1H NMR (CDCl3, 400 MHz): δ 8.08 (d, J=8.9 Hz, 2H), 6.98 (d, J=8.9 Hz, 2H), 4.64 (tt, J=7.7, 3.8 Hz, 1H), 3.95-4.09 (m, 2H), 3.64 (ddd, J=11.6, 8.2, 3.3 Hz, 2H), 2.01-2.13 (m, 2H), 1.78-1.93 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was treated with water
  3. extractionextracted with EA
  4. additionThe water layer was treated with 2N HCl to pH=3
  5. extractionThe water layer was then extracted with EA
  6. washThe organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-277b4dff213a4872b3749d4f4c51ebf3
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

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