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

HRID 1247723Notes

Reaction equation

HRID 1247723 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-benzyloxy-benzyl) 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-d93aa3f130ec4c34a5f7ccfe2c2caf51
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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