Thionyl Chloride → 4-(2-Benzyloxybenzyl)benzyl chloride

HRID 1982819Notes

Reaction equation

HRID 1982819 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][CH:21]=[CH:20][C:10]=1[CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][Cl:26])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 688722414-(2-Benzyloxybenzyl)benzyl alcohol

Product 1

HCID 219093154-(2-Benzyloxybenzyl)benzyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-Benzyloxybenzyl)benzyl alcohol (0.67 g) in dichloromethane (30 mL) was added thionyl chloride (0.48 mL), and the mixture was heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, to the residue was added water, and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was distilled to give 4-(2-benzyloxybenzyl)benzyl chloride (0.68 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure, to the residue
  4. additionwas added water
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled

Sources & evidence

ORD record
ord-b84dbe86f75442ada9899010b6ebeaeb
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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