2-tert-Butyl-4-methylphenol → HCID 178426895, compound

HRID 356824

Reaction equation

[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].C[Mg:14][Br:15]>C(OCC)C>[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:6]=1[O:12][Mg:14][Br:15])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

In an atmosphere of nitrogen, 16.42 g (100 mmol) of 2-tert-butyl-4-methylphenol was dissolved in 100 ml of diethyl ether and 33.3 ml of methylmagnesium bromide (100 mmol of diethyl ether solution) was added dropwise to this at 0° C. taking 5 minutes. After completion of the dropwise addition, the mixture was stirred at 25° C. for 10 minutes. After that, the diethyl ether was evaporated under vacuum, and 150 ml of toluene was added to obtain a toluene solution of 2-tert-butyl-4-methylphenoxymagnesium bromide. To the solution, 5.61 g (50 mmol) of 2-thiophenecarboxyaldehyde was added dropwise at 25° C. After stirring for 24 hours, 5% aqueous hydrochloric acid solution was added and aqueous layer was separated. After the organic layer was washed with a saturated aqueous sodium chloride solution, it was dried with anhydrous magnesium sulfate and the solvent was removed by evaporation. The residue was purified by a silica gel column chromatography (a developing solvent: hexane/ethyl acetate=30/1) to obtain 2-bis(2-hydroxy-3-tert-butyl-5-methylphenyl)methylthiophene in a yield of 63%.

Workup

additionAfter completion of the dropwise addition
customAfter that, the diethyl ether was evaporated under vacuum, and 150 ml of toluene
additionwas added

Sources & evidence

ORD record: ord-652e5f4fcaae48c0957b2b8d7ad406e5
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840646

Linked notes

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