Ethanol, 2-[(4-methylphenyl)sulfonyl]- → 3-Chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester

HRID 2182874Notes

Reaction equation

HRID 2182874 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[CH3:14])[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[C:15]1([CH3:27])[CH:20]=[CH:19][C:18]([S:21]([CH2:24][CH2:25]O)(=[O:23])=[O:22])=[CH:17][CH:16]=1>O=S(Cl)Cl>[C:15]1([CH3:27])[CH:20]=[CH:19][C:18]([S:21]([CH2:24][CH2:25][O:9][C:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([CH3:14])=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:6]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-HCID 2418593-(Chlorosulfonyl)-4-methylbenzoic acid

Product 1

HCID 865925683-Chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A heterogeneous mixture of 3-chlorosulfonyl-4-methylbenzoic acid (11.7 g, 50.0 mmol) in 18 mL of SOCl2 was refluxed for 3 h. After the excess of SOCl2 was removed, the residual brown oil was dissolved in 50 mL of CH3CN, and then 2-(p-tolylsulfonyl)ethanol (9.4 g, 47.0 mmol, 0.95 eq.) was added. The mixture was heated to reflux temperature for 24 h. Thereafter most of CH3CN was removed, the resulting oil was purified by short column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2) to give a light brown oil, which solidified on standing. The solid was dried further under vacuum to yield 19.5 g (99%) of 3-chlorosulfonyl-4-methylbenzoic acid 2-(p-tolylsulfonyl)ethyl ester (Intermediate 49).

Workup

  1. temperaturewas refluxed for 3 h
  2. customAfter the excess of SOCl2 was removed
  3. dissolutionthe residual brown oil was dissolved in 50 mL of CH3CN
  4. temperatureThe mixture was heated
  5. temperatureto reflux temperature for 24 h
  6. customThereafter most of CH3CN was removed
  7. customthe resulting oil was purified by short column chromatography (CH2Cl2 to 1% MeOH in CH2Cl2)
  8. customto give a light brown oil, which
  9. customThe solid was dried further under vacuum

Sources & evidence

ORD record
ord-3076bb806ddb4d4dab25ede020ca838b
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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