2-Iodobutane → HCID 69551882, compound

Temperature

65 °C

To 3-hydroxyphenyl acetic acid methyl ester (27.3 g, 165 mmol) in acetone (200 mL) was added 2-iodobutane (55 mL, 478 mmol) and potassium carbonate (83 g, 601 mmol). The mixture was heated at 65° C. for 48 hrs and filtered through a Celite® pad. The filtrate was concentrated in vacuo and the residue was diluted with dichloromethane and water. The aqueous phase was extracted with dichloromethane (3×100 mL). The combined extracts were washed with saturated sodium chloride (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford (3-sec-butoxy-phenyl)-acetic acid methyl ester. To a solution of (3-sec-butoxy-phenyl)-acetic acid methyl ester in methanol (200 mL) was added 10N sodium hydroxide solution (50 mL). The reaction mixture was stirred at 60° C. for 4 hrs. The solvent was evaporated and the mixture was acidified to pH=3 by addition of 6N hydrogen chloride solution. The aqueous phase was extracted with dichloromethane (3×100 m]L). The combined extracts were washed with saturated aqueous sodium chloride solution (80 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford (3-sec-butoxy-phenyl) acetic acid (25 g, 73% yield) as a light brown oil.

1. filtrationfiltered through a Celite® pad
2. concentrationThe filtrate was concentrated in vacuo
3. additionthe residue was diluted with dichloromethane and water
4. extractionThe aqueous phase was extracted with dichloromethane (3×100 mL)
5. washThe combined extracts were washed with saturated sodium chloride (50 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-5ce1b38e06974575a270ff29d1ea8f78

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07067529B2