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-f81d3c8448934979ad09d0f4db530a5a

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08343970B2