Chlorosulfonic acid → 4-Chlorosulfonyl-3-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester

HRID 2182886Notes

Reaction equation

[C:1]1([CH3:27])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:26])[CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH:23]([CH3:25])[CH3:24])[CH:17]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[Cl:28][S:29](O)(=[O:31])=[O:30]>C(Cl)Cl>[C:1]1([CH3:27])[CH:2]=[CH:3][C:4]([S:7]([CH2:10][CH2:11][O:12][C:13](=[O:26])[CH2:14][O:15][C:16]2[CH:21]=[C:20]([CH3:22])[C:19]([S:29]([Cl:28])(=[O:31])=[O:30])=[C:18]([CH:23]([CH3:24])[CH3:25])[CH:17]=2)(=[O:9])=[O:8])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 3-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 64, 5.5 g, 14.0 mmol) and 4 mL of CH2Cl2 was added dropwise chlorosulfonic acid (8.2 g, 70.0 mmol, 5.0 eq) with ice-bath cooling. The mixture was stirred at 0° C. for 3 h. The resulting thick oil was poured onto crushed ice with vigorous stirring. The mixture was extracted with EtOAc. The organic layer was washed with 1 N NaHCO3 solution, dried over MgSO4, and concentrated by evaporation to give crude product 4-chlorosulfonyl-3-isopropyl-5-methylphenoxyacetic acid 2-(toluene-4-sulfonyl)ethyl ester (Intermediate 65, 6.0 g, 87%) as light brown thick oil, which was purified by silica gel column chromatography.

Workup

temperaturecooling
additionThe resulting thick oil was poured
customonto crushed ice with vigorous stirring
extractionThe mixture was extracted with EtOAc
washThe organic layer was washed with 1 N NaHCO3 solution
dry with materialdried over MgSO4
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-1e3709f8188b46b1b0f74adfddde92aa
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897227B2

Reaction notes

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