Methanol → 4-(3-Pyridyloxymethyl)2-phenylbenzoic acid

HRID 2121165Notes

Reaction equation

HRID 2121165 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][C:5]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CO.[OH-].[K+]>O>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:24])=[O:2])=[C:5]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:6]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 106870984-(3-Pyridyloxymethyl)2-phenylbenzoic acid methyl ester

Product 1

HCID 234363704-(3-Pyridyloxymethyl)2-phenylbenzoic acidYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.60 g (8.14 mmol) of 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid methyl ester, prepared as in Example 187B, was added 15 mL of methanol, and a solution of 0.79 g (12 mmol) of 85% KOH in 3 mL of water. The mixture was stirred at reflux for 3 hours, then concentrated in vacuo. The residue was taken up in 5 mL of water and treated with 12 mL of 1M aqueous HCl. The precipitated product was filtered and washed with a small amount of water. The combined washings and filtrate were adjusted to pH 4 with 1M HCl, and additional precipitate was collected, then washed with water. The combined precipitates were dried in vacuo to give 4-(3-pyridyloxymethyl)-2-phenylbenzoic acid (2.48 g, 99%) as an off-white powder. 1H NMR (300 MHz, d6-DMSO) δ 5.31 (s, 2H), 7.31-7.56 (m, 9H), 7.76 (d, J=7.5 Hz, 1H), 8.19 (dd, J=1.0, 6.0 Hz, 1H), 8.39 (d, J=3.0 Hz, 1H), 12.8 (br s, 1H).

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationconcentrated in vacuo
  3. additiontreated with 12 mL of 1M aqueous HCl
  4. filtrationThe precipitated product was filtered
  5. washwashed with a small amount of water
  6. customwas collected
  7. washwashed with water
  8. customThe combined precipitates
  9. customwere dried in vacuo

Sources & evidence

ORD record
ord-de2a9c61682542be9857379d9ad52906
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

Loading…