Ethyl Acetate → HCID 57809137, compound

HRID 2105841Notes

Reaction equation

[CH3:1][S:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([O:14][CH2:15][CH3:16])[CH:4]=1.ClC1C=C(C=CC=1)C(OO)=[O:22].C(OCC)(=O)C>C(Cl)Cl>[CH2:15]([O:14][C:5]1[CH:4]=[C:3]([S:2]([CH3:1])=[O:22])[CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of ethyl 4-methylthio-2-ethoxybenzoate (1.1 g, 4.6 mmol) in methylene chloride (40 mL) was added 3-chloroperoxybenzoic acid (1.1 g, 4.5 mmol, 77%) in several portions. The reaction mixture was stirred at 0° C. for 15 min, after which TLC (50% ethyl acetate in hexanes) showed consumption of starting material. The reaction mixture was quenched with a solution of sodium thiosulfate and neutralize with a solution of sodium bicarbonate. The product was extracted three times with methylene chloride. The organic layer was washed with sodium bicarbonate, dried over magnesium sulfate, and concentrated. Purification of the crude residue by flash column chromatography (silica gel, eluting with 50% ethyl acetate in hexanes) gave ethyl 2-ethoxy-4-methanesulfinylbenzoate as a yellow oil (0.70 g, 58%). LC-MS: 257.2 [(M+H)+].

Workup

customconsumption of starting material
customThe reaction mixture was quenched with a solution of sodium thiosulfate
extractionThe product was extracted three times with methylene chloride
washThe organic layer was washed with sodium bicarbonate
dry with materialdried over magnesium sulfate
concentrationconcentrated
customPurification of the crude residue
washby flash column chromatography (silica gel, eluting with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-ae22a6338e104dc483d43789ff28575a
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579368B2

Reaction notes

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