Benzyl Chloride → 3-Benzyloxypyridine

HRID 556371Notes

Reaction equation

HRID 556371 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8](Cl)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>C(Cl)Cl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH2:8]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 79713-HydroxypyridineHCID 14798Sodium Hydroxide

Product 1

HCID 100126353-Benzyloxypyridine

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

9.5 g (10 mMol) 3-Hydroxy-pyridine and 9.45 ml (10 mMol) benzylchloride are dissolved in 50 ml CH2Cl2 at rt. 0.5 g Adogen 464® (Aldrich 63393-96-4) are added followed by dropwise addition of 50 ml of aq. NaOH solution (40% wt). The resulting yellow solution is stirred overnight, leading to formation of a white precipitate. The insolubles are filtered off and the filtrated is diluted with CH2Cl2 and H2O. The phases are separated and the aq. phase is repeatedly extracted with CH2Cl2. Combined organic extracts are dried, concentrated and the residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH 95:5) to give the title compound as a yellow oil: MS: [M+1]+=186; 1H MNR (CDCl3): δ ppm 8.42 (s, 1H), 8.26 (s, 1H), 7.55-7.38 (m, 5H), 7.30-7.19 (m, 2H), 5.17 (s, 2H).

Workup

  1. filtrationThe insolubles are filtered off
  2. additionthe filtrated is diluted with CH2Cl2 and H2O
  3. customThe phases are separated
  4. extractionthe aq. phase is repeatedly extracted with CH2Cl2
  5. customCombined organic extracts are dried
  6. concentrationconcentrated
  7. customthe residual crude product is purified by flash chromatography (SiO2, CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-929d45595c7d4b07b20fdfd4a687f445
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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