Bromoform → 2-(4-Isopropoxyphenyl)-2-methoxyacetic acid

An oven-dried flask was charged with 4-isopropoxybenzaldehyde (4.9 g, 29.9 mmol), anhydrous methanol (30 mL) and anhydrous dioxane (30 mL) then fitted with an addition funnel. The addition funnel was charged with a solution of KOH (8.4 g, 149.5 mmol) in anhydrous methanol (30 mL) and an aliquot (˜2 mL) was added to the reaction mixture. Bromoform (3.4 mL, 38.8 mmol) was added to the reaction mixture then the remaining KOH/MeOH solution was added dropwise over 10 minutes. After stirring for 18 hours, the mixture was concentrated in vacuo. The residue was diluted with water and the pH was adjusted to ˜2 using concentrated HCl then extracted with EtOAc. The combined organics were dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo gave 2-(4-isopropoxyphenyl)-2-methoxyacetic acid as a light yellow solid (6.8 g) which was used without further purification.

1. customthen fitted with an addition funnel
2. additionan aliquot (˜2 mL) was added to the reaction mixture
3. concentrationthe mixture was concentrated in vacuo
4. additionThe residue was diluted with water
5. extractionthen extracted with EtOAc
6. dry with materialThe combined organics were dried over Na2SO4
7. filtrationfiltered

ORD record

ord-dd44a53846e04641b8ee54bead7d800c

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685975B2