Sodium Hydroxide → 2-(Methoxycarbonyl)-3-[4-[2-(2-naphthoxy)ethoxy]phenyl]propionic acid

HRID 458722Notes

Reaction equation

HRID 458722 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][CH:20]([C:25]([O:27]C)=[O:26])[C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:24][O:23][C:21]([CH:20]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:30][CH:29]=1)[C:25]([OH:27])=[O:26])=[O:22]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10341401Dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylmalonate

Product 1

HCID 184429032-(Methoxycarbonyl)-3-[4-[2-(2-naphthoxy)ethoxy]phenyl]propionic acidYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 4-[2-(2-naphthoxy)ethoxy]benzylmalonate (0.44 g, 1.07 mmol) in a mixture of methanol (4.3 ml) and tetrahydrofuran (2.1 ml) at 0° C. is added a 2 mol/L aqueous solution of sodium hydroxide (0.59 ml, 1.18 mmol). The mixture is stirred for 2 h at room temperature, and then the solvent is removed under a vacuum. The residue was dissolved in saturated aqueous sodium bicarbonate (10 ml) and washed with ethyl acetate (10 ml). The aqueous solution is acidified to pH 2–3 with dilute hydrochloric acid and extracted with ethyl acetate (3×15 ml). The combined extracts are washed with water (20 ml) and brine (20 ml), dried over sodium sulfate, and concentrated. The residue is crystallized from ethyl acetate to give the title compound (0.35 g, 83%). HRMS calcd for C23H22O6: 394.4208. Found: 394.4206. MA calcd for C23H22O6: C, 70.04%; H, 5.62%. Found: C, 70.18%; H, 5.66%.

Workup

  1. customthe solvent is removed under a vacuum
  2. dissolutionThe residue was dissolved in saturated aqueous sodium bicarbonate (10 ml)
  3. washwashed with ethyl acetate (10 ml)
  4. extractionextracted with ethyl acetate (3×15 ml)
  5. washThe combined extracts are washed with water (20 ml) and brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-6b01b4b9d1374b1797f581277013c672
Source dataset
uspto-grants-2007_03
Patent number
US07192970B2

Reaction notes

Loading…