Thionyl Chloride → HCID 68468382, compound

HRID 1623615Notes

Reaction equation

HRID 1623615 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH2:18]O)[C:13]=1[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].S(Cl)([Cl:23])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([CH2:18][Cl:23])[C:13]=1[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68469285HCID 68469285, compound

Product 1

HCID 68468382HCID 68468382, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

19.8 g (0.058 mol, 1.0 eq.) of 4-decyloxy-2-hydroxymethyl-3-methylpyridine was dissolved in 300 mL of ethyl acetate, and 7.6 g (0.064 mol, 1.1 eq.) of thionyl chloride was added dropwise at 12 to 18° C. Subsequently, the mixture was allowed to react for 0.5 hours at room temperature, and then a 7% aqueous solution of sodium bicarbonate (220 g) was added to adjust the reaction liquid to pH 7.5. The organic layer was washed with a 5% aqueous solution of sodium bicarbonate (160 g), dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure, to obtain 15.8 g of 4-decyloxy-2-chloromethyl-3-methylpyridine as a black oily matter.

Workup

  1. customto react for 0.5 hours at room temperature
  2. customthe reaction liquid to pH 7.5
  3. washThe organic layer was washed with a 5% aqueous solution of sodium bicarbonate (160 g)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-cba6ad737e3d464a825847a3eeaaf739
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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