Benzenemethanol, 2-(phenylmethoxy)- → 1-(Benzyloxy)-2-(chloromethyl)benzene

HRID 743379

Reaction equation

HRID 743379 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.S(Cl)([Cl:19])=O>O1CCCC1.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[CH2:11][Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 18811Benzenemethanol, 2-(phenylmethoxy)-HCID 24386Thionyl Chloride

Product 1

HCID 5635071-(Benzyloxy)-2-(chloromethyl)benzene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The whole of the 2-benzyloxybenzyl alcohol thus obtained was dissolved in 500 ml of tetrahydrofuran, and 85 ml of thionyl chloride were added dropwise, whilst ice-cooling, to the resulting solution. The reaction mixture was then allowed to stand overnight at room temperature, after which it was concentrated by evaporation under reduced pressure to give a dark colored oil. This product was dissolved in toluene, and the solution was decolorized by treating it with silica gel for chromatography followed by filtration. The filtrate was concentrated by evaporation under reduced pressure to give 2-benzyloxybenzyl chloride as a yellow oil, which was used in the following reaction without further purification.

Workup

  1. temperaturecooling, to the resulting solution
  2. concentrationafter which it was concentrated by evaporation under reduced pressure
  3. customto give a dark colored oil
  4. additionby treating it with silica gel for chromatography
  5. filtrationfollowed by filtration
  6. concentrationThe filtrate was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-de01410fa79f49dd8e2a4f0cc6602f7b
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Linked notes

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