Hydrochloric Acid → 3-Methyl-1,3-dihydro-2-benzofuran-4-ol

HRID 527575Notes

Reaction equation

Cl.[CH3:2][CH:3]1[C:7]2[C:8]([O:12]COC)=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][O:4]1>CO.ClCCl>[CH3:2][CH:3]1[C:7]2[C:8]([OH:12])=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][O:4]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 8 ml vial 1-methyl-7-{[(methyloxy)methyl]oxy}-1,3-dihydro-2-benzofuran (Intermediate 97, 25.2 mg) was dissolved in methanol (1 ml) to give a colourless solution. A solution of HCl (2M/H2O) (0.259 ml, 0.519 mmol) was added. The reaction mixture was shaken at 80° C. After 30 minutes, the reaction mixture was diluted with 10 ml of dichloromethane. The phases were separated through a phase separator cartridge. The organic phase was mixed with the fraction obtained before and evaporated under vacuum to afford a residue which was purified by silica gel chromatography (Biotage SP1 system, 10 g-SNAP Silica column) with Cyclohexane/EtOAc as eluents (from 100/0 to 3/1 in 10 CV; then 3/1 for 5 CV; then from 3/1 to 1:1 in 5 CV; then 1:1 for 5 CV). The collected fractions afforded the title compound (24 mg).

Workup

customto give a colourless solution
customThe phases were separated through a phase separator cartridge
additionThe organic phase was mixed with the fraction
customobtained before and
customevaporated under vacuum
customto afford a residue which
customwas purified by silica gel chromatography (Biotage SP1 system, 10 g-SNAP Silica column) with Cyclohexane/EtOAc as eluents (from 100/0 to 3/1 in 10 CV

Sources & evidence

ORD record: ord-fc6f6402aec9438aaf39b95ec557de3c
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346790B2

Reaction notes

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