Dichloromethane → HCID 22479312, compound

HRID 1593234Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:6][C:7]=1C.[Cl:18][S:19]([OH:22])(=O)=[O:20].Cl[CH2:24]Cl>>[Cl:18][S:19]([C:7]1[C:6]([CH3:24])=[CH:5][C:4]([O:9][CH2:10][C:11]([CH3:16])([CH3:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:3][C:2]=1[CH3:1])(=[O:22])=[O:20]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 24638Chlorosulfonic acid

HCID 22479338HCID 22479338, compound2×

Product 1

HCID 22479312HCID 22479312, compoundYield 29%

Conditions

Temperature: -2 °C

Procedure

Methyl 3-(3,4-dimethylphenyloxy)-2,2-dimethylpropionate (Intermediate A8, 23.6 g, 0.100 mol) was added dropwise over 30 min to rapidly stirred chlorosulfonic acid (46.6 g, 0.400 mol) while the reaction temperature was maintained at −2° C. The reaction mixture was then poured into a stirred mixture of 300 g ice and 300 mL of dichloromethane. The aqueous phase was extracted with additional dichloromethane, and the combined organic layers were washed with water, 0.5 M sodium bicarbonate (X 2), and water. The solvent was removed at aspirator pressure and the residue ethyl acetate in hexanes) to yield 9.6 g (29%) of the title compound.

Workup

extractionThe aqueous phase was extracted with additional dichloromethane
washthe combined organic layers were washed with water, 0.5 M sodium bicarbonate (X 2), and water
customThe solvent was removed at aspirator pressure

Sources & evidence

ORD record: ord-cf1313ad95204746bf73a34d3b0c427c
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07294716B2

Reaction notes

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