Hydrochloric Acid → 2-(3-(Hydroxymethyl)phenyl)acetic acid

Temperature

80 °C

Calcium carbonate (11 g) was added to a mixture of ethyl[3-(bromomethyl)phenyl]acetate (4.56 g), dioxane (70 ml) and water (70 ml), followed by stirring at 80° C. for 6 hours. EtOAc and water were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc). The purified product thus obtained was mixed with EtOH (50 ml), and a 1M aqueous NaOH solution (35 ml) was added thereto, followed by stirring at room temperature for 1 hour. 1M hydrochloric acid (35 ml) was added to the reaction mixture, followed by concentration under reduced pressure. MeOH and Na2SO4 were added to the obtained residue, and the insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to obtain [3-(hydroxymethyl)phenyl]acetic acid (1.9 g).

1. dry with materialthe organic layer was dried over Na2SO4
2. concentrationconcentrated under reduced pressure
3. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)
4. customThe purified product thus obtained
5. stirringby stirring at room temperature for 1 hour
6. concentrationfollowed by concentration under reduced pressure
7. additionMeOH and Na2SO4 were added to the obtained residue
8. customthe insoluble matter was removed by filtration
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-24ec1bcbfa544c9ea678cc4aac849791

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051283B2