Hydrochloric Acid → HCID 4067614, compound

A 250 mL flask fitted with a stir-bar was charged with ethyl 3-isobutoxyphenoxyacetate (9.11 g, 36.1 mmol, 71% purity) and EtOH (100 mL). To the resultant solution was added KOH (4.05 g, 72.2 mmol) in H2O (15 mL). The mixture stirred 30 min at rt. 1M HCl was then added until a pH of 2.5 was reached. The mixture was concentrated in vacuo to 75 mL. NaOH (4 g) was added, and the solution was washed with CH2Cl2 (3×50 mL). 3M HCl was then added until a pH of 3 was attained, and the mixture was extracted with EtOAc (75 mL). The organic phase was washed with brine (50 mL), filtered through phase separation paper, and concentrated in vacuo to give 5.2 g of 72 as an off-white solid (64% from 71). 1H NMR (60 MHz, CDCl3): δ 11.4 (s, 1H), 7.3-7.0 (m, 1H), 6.7-6.3 (m, 3H), 4.6 (s, 2H), 3.7 (d, 2H), 2.0 (nonet, 1H), 1.0 (d, 6H) ppm. HPLC analysis (5:10:85 H2O:A1:MeOH) showed a purity of 95% with a retention time of 3.5 min.

1. customA 250 mL flask fitted with a stir-bar
2. concentrationThe mixture was concentrated in vacuo to 75 mL
3. additionNaOH (4 g) was added
4. washthe solution was washed with CH2Cl2 (3×50 mL)
5. addition3M HCl was then added until a pH of 3
6. extractionthe mixture was extracted with EtOAc (75 mL)
7. washThe organic phase was washed with brine (50 mL)
8. filtrationfiltered through phase separation paper
9. concentrationconcentrated in vacuo

ORD record

ord-84b48fc5b8b64814af0a5854f7453806

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08859780B2