Chlorosulfonic acid → Ethyl 4-chlorosulfonyl-2-methylphenoxyacetate

HRID 1991157Notes

Reaction equation

HRID 1991157 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([O:8][C:9](=[O:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[CH3:7]>>[CH2:6]([O:8][C:9](=[O:19])[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[CH3:18])[CH3:7]

Participants

3

Reactant 2

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

Product 1

HCID 11415129Ethyl 4-chlorosulfonyl-2-methylphenoxyacetateYield 91.7%

Procedure

An oven-dried 200 mL round-bottomed flask was charged with chlorosulfonic acid (18.5 mL, 167 mmol). Under N2 flow, compound 10.1 (29.3 g, 139 mmol) was added dropwise using a cannula tube at 0° C., and the reaction was stirred at room temperature for 1.5 h. The reaction mixture was poured into 300 mL of ice-water. Deposited crystals were collected, washed with 3×100 mL of ice-water, and dried in vacuo affording the title compound 10.2 (37.3 g). 1H NMR (300 MHz) (CDCl3) δ 7.86-7.84 (2H, m); 6.80 (1H, t, J=9.5 Hz); 4.76 (2H, s); 4.29 (2H, q, J=7.1 Hz); 2.37 (3H, s); 1.31 (3H, t, J=7.1 Hz).

Workup

  1. customat 0° C.
  2. customDeposited crystals were collected
  3. washwashed with 3×100 mL of ice-water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-7d45711d061049ebaa20d2589a0d7a43
Source dataset
uspto-grants-2010_01
Patent number
US07645779B2

Reaction notes

Loading…