Ethanol → HCID 59263298, compound

Temperature

90 °C

3-(3,5-difluorophenoxy)-5-(2-methoxy-1-methylethoxy)benzonitrile (1.00 equiv; 9.40 mmol; 3.00 g) was charged to a 100 ml round-bottomed flask (1 neck, condenser, magnetically stirred) with ethanol (515 mmol; 30.0 ml; 23.7 g). Water (138 mmol; 2.49 ml; 2.49 g), then sodium hydroxide (18.9M in water, 47.0 mmol; 2.49 ml; 3.75 g) was charged and the mixture heated to reflux (bath temperature 90° C.) for 4 hours. The mixture was cooled and solvent removed in vacuo affording a colourless solution (water not removed). The mixture was partitioned between water (50 ml) and MTBE (50 ml) and the layers separated (aqueous layer pH=14). The aqueous phase was acidified with HCl solution (2M, aq, 50 ml) and extracted with MTBE (50 ml). The organic layer was dried over MgSO4, filtered and the volatiles removed in vacuo affording 3-(3,5-difluorophenoxy)-5-(2-methoxy-1-methylethoxy)benzoic acid as a colourless oil (3.15 g, 99%).

1. temperaturethe mixture heated
2. temperatureThe mixture was cooled
3. customsolvent removed in vacuo
4. customaffording a colourless solution (water not
5. customremoved)
6. customThe mixture was partitioned between water (50 ml) and MTBE (50 ml)
7. customthe layers separated (aqueous layer pH=14)
8. extractionextracted with MTBE (50 ml)
9. dry with materialThe organic layer was dried over MgSO4
10. filtrationfiltered
11. customthe volatiles removed in vacuo

ORD record

ord-07f23ee2f0f94cd195edad51313e46e4

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700640B2