3-Pyridinemethanol → p-Isobutylphenylacetic acid-3-pyridylmethyl ester

HRID 26462

Reaction equation

HRID 26462 reaction equation
[Na].[OH:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.C[O:11][C:12](=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=1>O>[N:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][O:2][C:12](=[O:11])[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([CH3:22])[CH3:23])=[CH:16][CH:15]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 5360545SodiumHCID 10987436Methyl 2-(4-isobutylphenyl)acetate

Product 1

HCID 21323306p-Isobutylphenylacetic acid-3-pyridylmethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.05 g of sodium and 8 ml of 3-hydroxymethylpyridine was heated at 65°-70° C. for 10 hours. To this mixture was added 2.1 g of p-isobutylphenylacetic acid methyl ester, and the whole was heated at 95°-100° C. for 8 hours. After the reaction was complete, 100 ml of water was added. The resulting mixture was extracted with ether, and the ether layer separated was dehydrated and concentrated to leave an oily residue. This residue was distilled under reduced pressure to give 1.9 g of p-isobutylphenylacetic acid-3-pyridylmethyl ester as a colorless liquid, boiling at 142°-145° C./1 mmHg. Analysis-Calculated for C18H21NO2 : C, 76.29; H, 7.47; N, 4.94. Found: C, 76.02; H, 7.38; N, 4.79. Mass spectrum: parent ion 283 m/e.

Workup

  1. temperaturewas heated at 65°-70° C. for 10 hours
  2. temperaturethe whole was heated at 95°-100° C. for 8 hours
  3. extractionThe resulting mixture was extracted with ether
  4. customthe ether layer separated
  5. concentrationconcentrated
  6. customto leave an oily residue
  7. distillationThis residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-de71853288824c7a8387773f47f3f4dc
Source dataset
uspto-grants-1979_04
Patent number
US04150137

Linked notes

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