Chlorosulfonic acid → 4-Chlorosulfonyl-2-propylphenoxy-acetic acid ethyl ester

HRID 1991149Notes

Reaction equation

HRID 1991149 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([O:8][C:9](=[O:21])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19][CH3:20])[CH3:7]>>[CH2:6]([O:8][C:9](=[O:21])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:14][C:13]=1[CH2:18][CH2:19][CH3:20])[CH3:7]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acid2×HCID 20768112(2-Propyl-phenoxy)-acetic Acid Ethyl Ester

Product 1

HCID 207681244-Chlorosulfonyl-2-propylphenoxy-acetic acid ethyl esterYield 87.2%

Conditions

Temperature
0 °C

Procedure

Chlorosulfonic acid (36.59 mL, 550.5 mmol) was cooled to 0° C. under argon atmosphere. The cooled chlorosulfonic acid was added dropwise to compound 4.2 (24.5 g, 110.1 mmol) using a dropping funnel. The reaction was stirred at 0° C. for 30 min. and at room temperature for 4 h. The reaction mixture was poured into ice-water and stirred slowly at 0° C. for 20 min. The precipitated crystals were collected and dried in vacuo using oven at 40° C. to give 4.3 (30.8 g) as pale-yellow crystals. 1H NMR (300 MHz) (CDCl3) δ 7.90-7.79 (2H, m); 6.81 (1H, d, J=8.4 Hz); 4.75 (2H, s); 4.28 (2H, q, J=7.1 Hz); 2.79-2.67 (2H, m); 1.77-1.60 (2H, m); 1.30 (3H, t, J=7.1 Hz); 0.97 (3H, t, J=7.3 Hz).

Workup

  1. stirringstirred slowly at 0° C. for 20 min
  2. customThe precipitated crystals were collected
  3. customdried in vacuo
  4. customat 40° C.

Sources & evidence

ORD record
ord-c7e807e605274472b1702bbed0c11efb
Source dataset
uspto-grants-2010_01
Patent number
US07645779B2

Reaction notes

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