Sodium Hydroxide → 3-(4-Phenoxyphenyl)propanoic acid

HRID 386433Notes

Reaction equation

HRID 386433 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20213313Ethyl 3-(4-phenoxyphenyl)propanoate

Product 1

HCID 220365723-(4-Phenoxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of ethyl 3-(4-phenoxyphenyl)propanoate (S29, 500 mg, 1.95 mmol) in THF/MeOH (1/1, 8 mL) was treated with aqueous 4 N NaOH (0.5 mL) and was stirred for 20 h at 25° C. The reaction mixture was concentrated, diluted with aqueous 1 N HCl and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated to afford S30 (390 mg, 1.61 mmol, 82%) as a white solid: 1H NMR (CDCl3, 500 MHz) 7.34 (dd, 2H, J=8.4, 7.4 Hz), 7.18 (d, 2H, J=8.4 Hz), 7.10 (dt, 1H, J=7.7, 1.1 Hz), 7.00 (dd, 2H, J=8.8, 1.1 Hz), 6.95 (d, 2H, J=8.4 Hz), 2.96 (t, 2H, J=7.7 Hz), 2.70 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 179.2, 157.3, 155.6, 135.0, 129.7, 129.5, 123.1, 119.0, 118.7, 35.7, 29.8.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with aqueous 1 N HCl
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford S30 (390 mg, 1.61 mmol, 82%) as a white solid

Sources & evidence

ORD record
ord-6cafd303a38047b8b18091caf71cc16d
Source dataset
uspto-grants-2013_02
Patent number
US08372823B2

Reaction notes

Loading…