1,2-Ethanedithiol → Methyl 3-(3-hydroxyphenyl)-3-methylbutanoate

To a solution of methyl 3-(3-methoxyphenyl)-3-methylbutanoate 85.E (0.227 g, 1.02 mmol) in 1,2-dichloroethane (10 mL) was added 1,2-ethanedithiol (1.37 mL, 16.3 mmol) followed by aluminum chloride (1.09 g, 8.17 mmol) at 0° C. The reaction mixture was allowed to slowly warm to room temperature over four hours and was then quenched with saturated Rochelle's salt (potassium sodium tartrate) solution. The mixture was extracted (2×50 mL) with DCM. The combined organic layers were washed with water (1×40 mL) and brine (1×40 mL) and dried over magnesium sulfate. The filtrate was concentrated and the residue was purified by medium pressure chromatography (silica, 0 to 30% EtOAc:hexanes) to give methyl 3-(3-hydroxyphenyl)-3-methylbutanoate 85 (0.209 g, 98.3% yield). MS ESI (pos.) m/e: 226.0 (M+H2O)+.

1. customwas then quenched with saturated Rochelle's salt (potassium sodium tartrate) solution
2. extractionThe mixture was extracted (2×50 mL) with DCM
3. washThe combined organic layers were washed with water (1×40 mL) and brine (1×40 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationThe filtrate was concentrated
6. customthe residue was purified by medium pressure chromatography (silica, 0 to 30% EtOAc:hexanes)

ORD record

ord-d8f1041ae3da493ebb8cfbf1257ad20c

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030354B2