Hydrochloric Acid → HCID 117888980, compound

HRID 632516Notes

Reaction equation

HRID 632516 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[CH3:11].C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.Cl>CCOC(C)=O.C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:6][C:5]=1[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 12351986Methyl 4-hydroxy-2-methylbenzoate

Product 1

HCID 117888980HCID 117888980, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To 0.85 g of 4-hydroxy-2-methyl benzoic acid methyl ester were added 12 mL of acetonitrile, 2.12 g of K2CO3 and 0.84 g of 2-(chloromethyl)pyridine hydrochloride, and the mixture was stirred at 90° C. for 4 hours. The reaction mixture was allowed to cool back to room temperature and neutralized by the addition of 5% hydrochloric acid. To this, 150 mL of AcOEt was added, and the organic layer was separated. The obtained organic layer was washed with saturated brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography (hexane/AcOEt system) to give 1.18 g of the title compound (89% yield).

Workup

  1. temperatureto cool back to room temperature
  2. customthe organic layer was separated
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (hexane/AcOEt system)

Sources & evidence

ORD record
ord-851566d3a3354cc6a31d1aa3cf517101
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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