Thionyl Chloride → 2-(p-Toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoate

HRID 2182845Notes

Reaction equation

HRID 2182845 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].O=S(Cl)Cl.[C:20]1([CH3:32])[CH:25]=[CH:24][C:23]([S:26]([CH2:29][CH2:30]O)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[Cl:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:14][CH3:15])=[C:9]([CH:13]=1)[C:10]([O:12][CH2:30][CH2:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:32])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:11])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 1040075-Chlorosulphonyl-2-anisic acid2×

Product 1

HCID 224793622-(p-Toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chlorosulfonyl-2-methoxybenzoic acid (Intermediate 6, 3.0 g, 12.0 mmol) and SOCl2 (6 mL) was heated to reflux temperature for 2 h. Then excess SOCl2 was removed by distillation. The resulting residual oil was dissolved in 20 mL of CH2Cl2 and 2-(p-toluenesulfonyl)ethanol (available from Aldrich 2.0 g, 10 mmol) in 10 mL of CH2Cl2 was added at room temperature. The resulting mixture was heated to reflux temperature for 3 h. Thereafter volatile materials were removed under reduced pressure and the residual oil was purified by column chromatography (silica gel, hexane:CH2C2=1:1 to CH2Cl2) to give 3.5 g (81%) of 2-(p-toluenesulfonyl)ethyl 5-chlorosulfonyl-2-methoxybenzoate (Intermediate 7) as clear thick oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 2 h
  3. customThen excess SOCl2 was removed by distillation
  4. dissolutionThe resulting residual oil was dissolved in 20 mL of CH2Cl2
  5. temperatureThe resulting mixture was heated
  6. temperatureto reflux temperature for 3 h
  7. customThereafter volatile materials were removed under reduced pressure
  8. customthe residual oil was purified by column chromatography (silica gel, hexane:CH2C2=1:1 to CH2Cl2)

Sources & evidence

ORD record
ord-ba40d2f2c684407687619a106ab4e900
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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