Pyridine → 1-(Benzyloxy)-2-(chloromethyl)benzene

HRID 256413

Reaction equation

HRID 256413 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OC1C=CC=CC=1CO.C([Cl:33])C1C=CC=CC=1.CC(C)([O-])C.[K+].N1C=CC=CC=1.S(Cl)(Cl)=O>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][Cl:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 1049PyridineHCID 5146Salicyl AlcoholHCID 7503Benzyl ChlorideHCID 18811Benzenemethanol, 2-(phenylmethoxy)-HCID 24386Thionyl ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 5635071-(Benzyloxy)-2-(chloromethyl)benzeneYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of 46.5 (0.217 mole) 2-benzyloxybenzyl alcohol (prepared by reaction of 2-hydroxybenzyl alcohol with benzyl chloride in ethanol containing an equimolar amount of potassium t-butoxide at 100° C.) in 100 ml chloroform was added 17.2 g (0.217 mole) pyridine followed by dropwise addition of a solution of 25.8 g (0.217 mole) thionyl chloride in 60 ml chloroform. The resulting mixture was heated at reflux for 1.5 hours, cooled, washed with water, brine and dried (MgSO4). Evaporation of solvent gave 45.8 g crude oil which was distilled in vacuo to yield 40.7 g (81%) of product as a colorless oil, b.p. 141° C.(1 Torr).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of solvent
  7. customgave 45.8 g crude oil which
  8. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-e57e3edb022740a8926893137e99290e
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Linked notes

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