Hydrochloric Acid → Methyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate

Temperature

-10 °C

To 2-(3,4-dimethoxyphenyl)-2-hydroxyacetonitrile (1.25 g, 6.48 mmol) in ether (20 mL) and MeOH (1.5 mL) at −10° C. was added 4N HCl in dioxane (6 mL, 24 mmol). The reaction was stirred at −10° C. for 1 h, then stored at 4° C. for 2 days. The reaction was filtered, and washed with ether. The solid was dissolved in water (15 mL) and CH2Cl2 (15 mL) and stirred for 1 h. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3×20 mL), dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes) to provide 6B (1.35 g, 92%). LC-MS: 249.16 (M+Na)+.

1. waitstored at 4° C. for 2 days
2. filtrationThe reaction was filtered
3. washwashed with ether
4. dissolutionThe solid was dissolved in water (15 mL)
5. stirringCH2Cl2 (15 mL) and stirred for 1 h
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with CH2Cl2 (3×20 mL)
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting residue was purified via silica gel chromatography (0-60% ethyl acetate/hexanes)

ORD record

ord-0f3695f7d46346db8c8403bdaf714eb3

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08044242B2