Sodium hydride → tert-Butyl (4-tert-butyl-3-methoxyphenoxy)acetate

HRID 1350819

Reaction equation

[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[O:14][CH3:15])([CH3:6])([CH3:5])[CH3:4].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:9][C:8]=1[O:14][CH3:15])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 60% sodium hydride (96 mg, 2.4 mmol) in tetrahydrofuran (THF) (10 ml) was added 4-tert-butyl-3-methoxyphenol (360 mg, 2 mmol) at 0° C., followed by additional stirring for 30 minutes. Then, tert-butyl bromoacetate (468 mg, 2.4 mmol) was added and the mixture was refluxed at 80° C. for 1 hour. The reaction was then quenched with saturated aqueous solution of ammonium chloride and the crude product was extracted with ethylacetate. The organic layer was separated, washed with brine, dried over magnesium sulfate. Then, filtration, evaporation to remove the solvent under reduced pressure gave the residue, which was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and ethylacetate (20/1 to 4/1) to furnish 466 mg (79% yield) of the title compound as a white solid.

Workup

customThe reaction was then quenched with saturated aqueous solution of ammonium chloride
extractionthe crude product was extracted with ethylacetate
customThe organic layer was separated
washwashed with brine
dry with materialdried over magnesium sulfate
filtrationThen, filtration, evaporation
customto remove the solvent under reduced pressure
customgave the residue, which
washeluted with a volume mixture of hexane and ethylacetate (20/1 to 4/1)

Sources & evidence

ORD record: ord-b7e96e3207f6426ca9545b444befa29f
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07214824B2

Linked notes

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