Chlorosulfonic acid → Ethyl 4-chlorosulfonyl-2-methylphenoxyacetate

HRID 1744414Notes

Reaction equation

HRID 1744414 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][C:7]1[CH:19]=[CH:18][CH:17]=[CH:16][C:8]=1[O:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]>>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:9][C:8]1[CH:16]=[CH:17][C:18]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:19][C:7]=1[CH3:6])[CH3:15]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 3022879Ethyl 2-(2-methylphenoxy)acetate

Product 1

HCID 11415129Ethyl 4-chlorosulfonyl-2-methylphenoxyacetate

Conditions

Temperature
4 °C

Procedure

To a flask containing chlorosulfonic acid (15.0 mL, 226 mmol) at 4° C. was added ethyl (2-methylphenoxy)acetate A1a (10.0 g, 51.6 mmol) slowly. The mixture was stirred at 4° C. for 30 min and room temperature for 2 h, and then poured into ice water. The precipitated white solid was filtered, washed with water, and dried under vacuum overnight to provide 14.0 g (93%) of A1b as a white solid; 1H NMR (300 MHz, CDCl3) δ 7.87–7.84 (m, 2 H), 6.80 (d, J=9.5 Hz, 1 H), 4.76 (s, 2 H), 4.29 (q, J=7.1 Hz, 2 H), 2.37 (s, 3 H), 1.31 (t, J=7.1 Hz, 3 H); MS (ES) m/z: 315 (M+Na+).

Workup

  1. filtrationThe precipitated white solid was filtered
  2. washwashed with water
  3. customdried under vacuum overnight
  4. customto provide 14.0 g (93%) of A1b as a white solid

Sources & evidence

ORD record
ord-994e4878acce45ba91ba60e61a599d45
Source dataset
uspto-grants-2006_03
Patent number
US07015329B2

Reaction notes

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