Benzyl Alcohol → Dibenzyl ether

HRID 22157

Reaction equation

HRID 22157 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12](S(O)(=O)=O)=[CH:11][CH:10]=1>O1CCCC1.CN(C)C=O>[CH2:1]([O:8][CH2:19][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 244Benzyl AlcoholHCID 6101p-Toluenesulfonic acid

Product 1

HCID 7657Dibenzyl ether

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a manner similar to that described in Example I, 0.68 ml of benzyl alcohol and 7 mg of p-toluenesulfonic acid are added to a solution of 350 mg of Compound Z-1(DMTD) in a mixture of 7 ml of tetrahydrofuran and 3 ml of dimethylformamide and the mixture stirred at room temperature for 24 hours. At the end the volatiles are removed in vacuo to obtain a residue which is purified on a preparative HPLC column using water/acetonitrile (40/60) as eluant. The appropriate fractions are combined and lyophilized to obtain benzyl ether of Z-1(DMTD).

Workup

  1. customAt the end the volatiles are removed in vacuo
  2. customto obtain a residue which
  3. customis purified on a preparative HPLC column

Sources & evidence

ORD record
ord-1454dbbd4a4c45a6b9416b9307ef6d28
Source dataset
uspto-grants-1995_06
Patent number
US05428009

Linked notes

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