Water → HCID 23549386, compound

HRID 1708499Notes

Reaction equation

HRID 1708499 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 23549386HCID 23549386, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-hydroxyphenylacetic acid methyl ester (8.4 g; 50 mmol) in DMF (100 ml)were added potassium carbonate (14.0g; 100 mmol) and 2-chloromethylpyridine hydrochloride (8.2 g; 50 mmol), and the resulting mixture was stirred at 50° C. for 24 h. The mixture was then poured into water, extracted with ethyl acetate, the acetate layer was washed with water, brine and concentrated in vacuo. The residue was purified on silica gel column (hexane-ethyl acetate 1:1) to provide 9.5 g of 4-(2-pyridylmethoxy)phenylacetic acid methyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe acetate layer was washed with water, brine
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on silica gel column (hexane-ethyl acetate 1:1)

Sources & evidence

ORD record
ord-f6bb9329708741ddb95239d8cd1ba372
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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