Thionyl Chloride → 4-(Benzyloxy)benzene-1-sulfonyl chloride

HRID 643987Notes

Reaction equation

HRID 643987 reaction equation
S(Cl)([Cl:3])=O.[Na+].[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O-:23])(=O)=[O:21])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C=O)C>[CH2:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([Cl:3])(=[O:23])=[O:21])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 23685655Sodium p-benzyloxybenzenesulfonate

Product 1

HCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Thionyl chloride (200 mL, 326.2 grams, 2742 mmol) is added to the solid title A compound, 4-benzyloxybenzenesulfonic acid sodium salt, followed by 10 drops of DMF. The mixture is heated to reflux overnight and then concentrated under vacuum. Hot toluene (250 mL) is added, and the mixture is filtered. The filtrate is concentrated under vacuum. Toluene is again added to the residue followed by filtration and concentration under vacuum to give 4-benzyloxybenzenesulfonyl chloride as a white solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated under vacuum
  4. additionHot toluene (250 mL) is added
  5. filtrationthe mixture is filtered
  6. concentrationThe filtrate is concentrated under vacuum
  7. additionToluene is again added to the residue
  8. filtrationfollowed by filtration and concentration under vacuum

Sources & evidence

ORD record
ord-93e94bfbd5a040bf9a50fc7449853313
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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