Thionyl Chloride → HCID 68466606, compound

HRID 1623613Notes

Reaction equation

HRID 1623613 reaction equation
[CH2:1]([O:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:17]O)[C:12]=1[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].S(Cl)([Cl:22])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([O:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][Cl:22])[C:12]=1[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 68469848HCID 68469848, compound

Product 1

HCID 68466606HCID 68466606, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

16.0 g (0.05 mol, 1.0 eq.) of 4-nonyloxy-2-hydroxymethyl-3-methylpyridine was dissolved in 320 mL of ethyl acetate, and 6.5 g (0.055 mol, 1.1 eq.) of thionyl chloride was added dropwise at 8 to 12° C. Subsequently, the mixture was allowed to react for 0.5 hours at room temperature, and then a 7% aqueous solution of sodium bicarbonate (200 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 12.8 g of 4-nonyloxy-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-e0e878ce877d487baf3146617bc7e396
Source dataset
uspto-grants-2014_07
Patent number
US08778975B2

Reaction notes

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