Sodium Hydroxide → 3-(4-Fluorophenyl)pentanedioic acid

An aqueous solution of sodium hydroxide (3N, 23 mL, 69 mmol) was added to a solution of 2-(4-fluorophenyl)-1,1,3-trimethoxy carbonyl propane (6.7 g, 21.5 mmol) in methanol (100 ml) at room temperature and the mixture was stirred for 12 hours. The resulting mixture was concentrated under reduced pressure, and then water (20 ml) and concentrated hydrochloric acid (10 ml) were added under ice cooling. The aqueous mixture was refluxed for 12 hours. The reaction mixture was extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from ethyl acetate-hexane to obtain 4.5 g of 3-(4-fluorophenyl) glutaric acid (yield 93%). mp. 145–147° C.

1. concentrationThe resulting mixture was concentrated under reduced pressure
2. additionwater (20 ml) and concentrated hydrochloric acid (10 ml) were added under ice cooling
3. temperatureThe aqueous mixture was refluxed for 12 hours
4. extractionThe reaction mixture was extracted with ethyl acetate
5. extractionThe organic extract
6. washwas washed with water and saturated sodium chloride
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was removed under reduced pressure
9. customthe residue was crystallized from ethyl acetate-hexane

ORD record

ord-5ac5d3ef3b7e47bc9428cb7402a0f45b

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07208495B2