Pyridine → 2-(Chloromethyl)anisole

HRID 1374833Notes

Reaction equation

HRID 1374833 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]O.[Cl:11]C(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5][Cl:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 691542-Methoxybenzyl alcoholHCID 94429Triphosgene

Product 1

HCID 814952-(Chloromethyl)anisoleYield 290.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Methoxybenzyl alcohol (1.01 g, 7.31 mmol) and triphosgene (757 mg, 2.55 mmol) were dissolved in tetrahydrofuran (5 ml). The solution was added with pyridine (1.18 ml, 14.6 mmol) under ice cooling, and then warmed to room temperature. After 20 minutes, insoluble solids were removed by filtration, and the solvent was evaporated under reduced pressure. The resulting oil was diluted with ethyl acetate and insoluble solids were further removed. The solvent was evaporated under reduced pressure to obtain the title compound as pale yellow oil (1.16 g, yield: 100%).

Workup

  1. custominsoluble solids were removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe resulting oil was diluted with ethyl acetate and insoluble solids
  4. customwere further removed
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-71dba6b8c3ad4a27968588eb0b02140f
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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