tert-Butanol → 4,6-Di-tert-butyl-5-hydroxy-2-methylbenzofuran

HRID 1900514Notes

Reaction equation

CS(O)(=O)=O.[C:6]([C:10]1[C:15]2[CH:16]=[C:17]([CH3:19])[O:18][C:14]=2[CH:13]=[CH:12][C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7].[C:21](O)([CH3:24])([CH3:23])[CH3:22].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:6]([C:10]1[C:15]2[CH:16]=[C:17]([CH3:19])[O:18][C:14]=2[CH:13]=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:11]=1[OH:20])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonic acid (1.2 ml) was added dropwise to a chloroform solution of 4-tert-butyl-5-hydroxy-2-methylbenzofuran (250 mg, 1.2 mmol) and tert-butyl alcohol (500 mg, 6.0 mmol) under cooling with ice. After stirring at 0° C. for 15 min, the mixture was poured into ice water. The mixture was then neutralized with 1N aqueous sodium hydroxide and subjected to extraction with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (n-hexane) to afford 4,6-di-tert-butyl-5-hydroxy-2-methylbenzofuran (35 mg) as a pale yellow oil. Mass 260(M+), 245, 57

Workup

temperatureunder cooling with ice
extractionsubjected to extraction with ethyl acetate
washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customThe concentrate was purified by silica gel chromatography (n-hexane)

Sources & evidence

ORD record: ord-d18e2f867ac44d57930fe873784ee504
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574178

Reaction notes

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