Water → Ethyl 4-(2,3-dimethylphenoxy)butyrate

HRID 1670060Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([O:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16]Br)[CH3:11].[H-].[Li+].O>CS(C)=O>[CH2:10]([O:12][C:13](=[O:18])[CH2:14][CH2:15][CH2:16][O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,3-dimethylphenol (25 g, 204 mmol) in DMSO (205 mL) was added 4-bromo-butyric acid ethyl ester (40.96 g, 210 mmol) and lithium hydride (2.0 g, 250 mmol) at room temperature. The resulting light brown solution was stirred for 2 days. Then, the reaction mixture was cooled to 0° C. and water (200 mL) was added slowly. The organic compound was extracted into hexanes (2×200 mL). The combined organic extracts were washed with brine solution (150 mL) and the organic solution was dried over anhydrous magnesium sulfate. Filtration of the drying agent and the removal of the solvent gave light brown oil. The crude mixture was purified by using a Biotage™ (40 L) column chromatography eluting with 5% ethyl acetate in hexanes to isolate 4-(2,3-dimethyl-phenoxy)-butyric acid ethyl ester (45.32 g, 94%) as a colorless oil: ES(+)-HRMS m/e calculated for C14H20O3 (M+)+ 236.1412, found 236.1419.

Workup

extractionThe organic compound was extracted into hexanes (2×200 mL)
washThe combined organic extracts were washed with brine solution (150 mL)
dry with materialthe organic solution was dried over anhydrous magnesium sulfate
filtrationFiltration of the drying agent
customthe removal of the solvent
customgave light brown oil
customThe crude mixture was purified
washeluting with 5% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-834a2de8dc1342bf87a39444739fa9e3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989454B2

Reaction notes

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