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

HRID 1826629Notes

Reaction equation

HRID 1826629 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, water was added to the residue, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure 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, water
  4. additionwas added to the residue
  5. extractionthe resulting mixture was extracted with diethyl ether
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6e4e47dd66a04a5297aa79782827313e
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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