Pyridine → 2-(3-Chloropropyl)-6-methylphenol

HRID 343484Notes

Reaction equation

HRID 343484 reaction equation
O[CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12].N1C=CC=CC=1.S(Cl)([Cl:21])=O>O1CCCC1.CN(C)C=O>[Cl:21][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[OH:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 543527972-(3-Hydroxypropyl)-6-methylphenol

Product 1

HCID 544438172-(3-Chloropropyl)-6-methylphenol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(3-hydroxypropyl)-6-methylphenol (3.0 g) in tetrahydrofuran (30 mL) were added pyridine (730 μL), thionyl chloride (2 mL) and one drop of N,N-dimethylformamide. After stirring at 60° C. for 2 hours, the reaction mixture was evaporated, and then diethyl ether was added to the residue. The resulting solution was washed with distilled water and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo to give the title compound in quantitative yield.

Workup

  1. customthe reaction mixture was evaporated
  2. additiondiethyl ether was added to the residue
  3. washThe resulting solution was washed with distilled water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d12eb7ad3b8d4622b4cc040d6ed8f77d
Source dataset
uspto-grants-1999_01
Patent number
US05861437

Reaction notes

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