Methyl Salicylate → HCID 18508033, compound

HRID 558167Notes

Reaction equation

HRID 558167 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl.Cl[CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([O:10][CH3:11])=[O:9])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chloride

Product 1

HCID 18508033HCID 18508033, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl salicylate (10 g, 66 mmol) and 4-chloromethylpyridine hydrochloride (11 g, 67 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (19 g, 140 mmol) under ice-cooling, and then the mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured into an ice water and the aqueous layer was extracted with ethyl acetate (150 mL, twice). The ethyl acetate layer was washed with a saturated brine solution (200 mL), dried over anhydrous sodium sulfate, and concentrated under a reduced pressure to dryness, and the resultant residue was purified with a silica gel column chromatography (hexane/ethyl acetate) and dried to give 12 g (75%) of the titled compound as a colorless solid.

Workup

  1. temperaturecooling
  2. extractionthe aqueous layer was extracted with ethyl acetate (150 mL
  3. washThe ethyl acetate layer was washed with a saturated brine solution (200 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under a reduced pressure to dryness
  6. customthe resultant residue was purified with a silica gel column chromatography (hexane/ethyl acetate)
  7. customdried

Sources & evidence

ORD record
ord-5211e9108a8e4995aab106b65d56fc73
Source dataset
uspto-grants-2011_11
Patent number
US08063034B2

Reaction notes

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