Thionyl Chloride → 5-(Chlorosulfonyl)-2-ethoxybenzoic acid

HRID 618803Notes

Reaction equation

HRID 618803 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].S(Cl)(Cl)=O.[Cl:17][S:18](O)(=[O:20])=[O:19]>O>[Cl:17][S:18]([C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7])(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 24638Chlorosulfonic acidHCID 672522-Ethoxybenzoic acid

Product 1

HCID 113800715-(Chlorosulfonyl)-2-ethoxybenzoic acidYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Molten 2-ethoxybenzoic acid (25.0 g, 0.150 mol) was added to a stirred, ice-cooled mixture of thionyl chloride (11 ml, 0.151 mol) and chlorosulphonic acid (41.3 ml, 0.621 mol), whilst maintaining the temperature of the reaction mixture below 25° C. The resulting mixture was stirred at room temperature for 18 hours and then poured into a stirred mixture of ice (270 g) and water (60 ml) to give an off-white precipitate. Stirring was continued for 1 hour, then the product was collected by filtration, washed with water and dried under vacuum to provide the title compound (36.08 g). A reference sample, m.p. 115-116° C., was obtained by crystallisation from hexane:toluene. Found: C,41.02; H,3.27. C9H9ClO5S requires C,40.84; H,3.43%. δ (CDCl3): 1.64(3H,t), 4.45(2H,q), 7.26(1H,d), 8.20(1H,dd), 8.80(1H,d).

Workup

  1. temperaturecooled
  2. temperaturewhilst maintaining the temperature of the reaction mixture below 25° C
  3. customto give an off-white precipitate
  4. stirringStirring
  5. waitwas continued for 1 hour
  6. filtrationthe product was collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-bc7c8c0f8cc5458a9618c1eb53a8303b
Source dataset
uspto-grants-1999_09
Patent number
US05955611

Reaction notes

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