Hydrochloric Acid → 3-(4-Chlorosulfonyl-phenyl)-acrylic acid

HRID 226168Notes

Reaction equation

HRID 226168 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([OH:16])(=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>>[Cl:1][S:2]([C:12]1[CH:13]=[CH:14][C:9]([CH:8]=[CH:7][C:6]([OH:16])=[O:15])=[CH:10][CH:11]=1)(=[O:5])=[O:3]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 87842-Propenoic acid, 3-phenyl-HCID 24638Chlorosulfonic acid

Product 1

HCID 38309693-(4-Chlorosulfonyl-phenyl)-acrylic acidYield 20.3%

Conditions

Temperature
41 °C

Procedure

To neat chlorosulfonic acid (5.3 ml, 80 mmol) at 0-5° C. temperature slowly cinnamic acid (41) (1.47 g, 10 mmol) was added. As the reaction proceeded hydrogen chloride gas evolved. The reaction mixture was stirred successively at 0° C. for 1 hour, at ambient temperature for 2 hours and at 40-42° C. for 2 hours. The dark, viscous syrup was poured onto ice, the precipitated solid was filtered and washed with water. The title compound (0.5 g, 20%) as a white solid was obtained. 1H NMR (DMSO-d6, HMDSO), δ: 6.55 (1H, d, J=16 Hz); 7.58 (1H, d, J=16.0 Hz); 7.65 (4H, s); 8.15 (1H, br s).

Workup

  1. additionThe dark, viscous syrup was poured onto ice
  2. filtrationthe precipitated solid was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-23c6f8faa9c942ee822c9b3bc9347514
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

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