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

HRID 1013058Notes

Reaction equation

HRID 1013058 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 acid

Conditions

Temperature
42 °C

Procedure

To neat chlorosulfonic acid (26.5 mL, 0.4 mol) at 18° C. temperature slowly cinnamic acid (7) (7.35 g, 0.05 mol) was added. As the reaction proceeded, hydrogen chloride gas evolved. The reaction mixture was stirred successively at 20° C. for 3 hours and at 42° C. for 3 hours. The dark, viscous syrup was poured into ice water, and the precipitated solid was filtered and washed with water. The title compound was obtained (6.8 g, 55%) as a white solid. 1H NMR (DMSO-d6, HMDSO), δ: 6.55 (1H, d, J=16.0 Hz); 7.58 (1H, d, J=16.0 Hz); 7.65 (4H, s); 8.15 (1H, br s).

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-e0a34d80fa194bf995317b3de811db62
Source dataset
uspto-grants-2011_07
Patent number
US07981895B2

Reaction notes

Loading…