Water → 2-(4-(Chlorosulfonyl)-3,5-dimethylphenoxy)acetic acid

HRID 628153Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[O:5][CH2:6][C:7]([OH:9])=[O:8].[Cl:14][S:15](O)(=[O:17])=[O:16].O.C1COCC1>C(Cl)Cl>[Cl:14][S:15]([C:12]1[C:11]([CH3:13])=[CH:10][C:4]([O:5][CH2:6][C:7]([OH:9])=[O:8])=[CH:3][C:2]=1[CH3:1])(=[O:17])=[O:16]

Participants

Conditions

Temperature: 0 °C

Procedure

Referring to FIG. 37, to a solution of 2-(3,5-dimethylphenoxy)acetic acid (13 g, 72 mmol) in DCM (130 mL) was added dropwise a solution of ClSO3H (19.2 g, 166 mmol) in DCM (20 mL) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 h. Water (100 mL) and THF (30 mL) were added and the resulting mixture was stirred for 5 min The two layers were separated and the organic layer was washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give product as a white solid (6 g, 30% yield); 1H NMR (CDCl3, 300 MHz): δ 6.79 (s, 2H), 4.79 (s, 2H), 2.77 (s, 6H).

Workup

stirringthe resulting mixture was stirred for 5 min The two layers
customwere separated
washthe organic layer was washed with brine (100 mL)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-69cb46b93e624423b2c9f4b7600994cd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309283B2

Reaction notes

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