Phenol → HCID 53948539, compound

HRID 1614570Notes

Reaction equation

HRID 1614570 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[O:19][C:20]1[C:25]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:23]=[CH:22][N:21]=1>CN(C=O)C>[O:7]([CH2:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[O:19][C:20]1[C:25]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:23]=[CH:22][N:21]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 54494619HCID 54494619, compound

Product 1

HCID 53948539HCID 53948539, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

Phenol (0.16 g) and potassium carbonate (0.12 g) were stirred together in DMF (6 ml) under nitrogen at room temperature. After 20 minutes, a solution of methyl 2-(3-chloromethylphenoxy)-3-pyridinylacetate (0.5 g) in DMF was added and stirring continued. Copper-bronze (cat.) was added and the reaction mixture heated at 100° C. for a total of 5 hours. GC analysis indicated complete reaction. The reaction mixture was cooled and filtered, and then poured into water (50 ml). The aqueous mixture was extracted with ether (× 3) and the combined extracts washed with dilute sodium hydroxide solution. The ether solution was the dried, filtered and evaporated to give methyl 2-(3-phenoxymethylphenoxy)-3-pyridinylacetate as a yellow oil (0.35 g, 59%), mass spectrum m/e 349 (M+); 1H NMR (CDCl3) inter alia delta 3.69 (3H, s); 3.76 (2H, s); 5.07 (2H, s) ppm, contained with traces of DMF. In a separate experiment, the chloromethyl compound (2.73 g, prepared as above) yielded a further 2.00 g of methyl 2-(3-phenoxymethylphenoxy)-3-pyridinylacetate.

Workup

  1. customreaction
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. additionpoured into water (50 ml)
  5. extractionThe aqueous mixture was extracted with ether (× 3)
  6. washthe combined extracts washed with dilute sodium hydroxide solution
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6fb74ab53d04477cbfe847f5054c5db1
Source dataset
uspto-grants-1993_03
Patent number
US05198444

Reaction notes

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