Thionyl Chloride → HCID 66876006, compound

HRID 1666494Notes

Reaction equation

HRID 1666494 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]([CH2:15]O)[CH:12]=[CH:13][CH:14]=2)[CH:3]=1.S(Cl)([Cl:19])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:19][CH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 66875762HCID 66875762, compound

Product 1

HCID 66876006HCID 66876006, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(4-Methyl-pyridin-2-yloxy)-phenyl]-methanol from Step 1 (4.75 g, 22.1 mmol), in dichloromethane (50 mL), was cooled to 0° C., and treated dropwise with thionyl chloride (1.93 mL, 26.5 mmol). The reaction mixture was allowed to warm to ambient temperature and was stirred for 3 h. Saturated aqueous sodium bicarbonate (20 mL) was added and the mixture was stirred at rt for 5 min. The organic layer was separated, dried over sodium sulfate, filtered and concentrated by evaporation to afford the desired product (5.16 g, 99% yield) as an oil.

Workup

  1. stirringthe mixture was stirred at rt for 5 min
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-45f6cd7ced714848b4d99ed0c13b1bdf
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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