Lithium Hydroxide → 3-Methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoic acid

Temperature

60 °C

Methyl 3-methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoate (crude from Step 1) was dissolved in THF (5 mL) and a suspension of LiOH (550 mg, 23 mmol) in water (5 mL) was added. The mixture was stirred vigorously and heated at 60° C. for 6 h before it was concentrated to half volume. Water (5 mL) was added and the mixture was extracted with diethyl ether (1×10 mL). The aqueous layer was acidified with 4N HCl to pH 2. The resulting mixture was extracted with ethyl acetate (3×10 mL) and the combined organics were washed (1×10 mL H2O, 1×10 mL brine), dried over MgSO4 and evaporated to give 3-methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoic acid (1.0 g, 82%) as a white solid. ESI-MS m/z calc. 280.1, found 281.3 (M+1)+; Retention time: 1.34 minutes (3 min run).

1. additionwas added
2. concentrationwas concentrated to half volume
3. additionWater (5 mL) was added
4. extractionthe mixture was extracted with diethyl ether (1×10 mL)
5. extractionThe resulting mixture was extracted with ethyl acetate (3×10 mL)
6. washthe combined organics were washed (1×10 mL H2O, 1×10 mL brine)
7. dry with materialdried over MgSO4
8. customevaporated

ORD record

ord-bf90b161665247c99acf0800a924b1c1

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365588B2