Hydrochloric Acid → HCID 178525563, compound

Temperature

40 °C

To a round 25 ml bottomed flask containing cis-methyl [4-(2,4-dihydroxyphenyl)cyclohexyl]acetate (10 mg, 0.038 mmol) and water (4 ml) was added sodium hydroxide (5 mg, 0.13 mmol) and the solution heated to 40° C. for 1 hr. The solution was poured into a separating funnel containing ethyl acetate (15 ml) and water (10 ml). To the aqueous layer was then added aqueous hydrochloric acid (10 ml, 1.0M) and ethyl acetate (20 ml). The layers were separated and the aqueous layer extracted with ethyl acetate (3×10 ml). The combined organic extracts were washed with brine (15 ml), dried over magnesium sulfate, filtered and concentrated in vacuo affording the title compound (5 mg, 55%) as a solid. m/z (ES+) 251 (M+H+); δH(CD3OD) 1.61-1.77 (8H, m), 2.30 (1H, m), 2.49 (2H, d), 2.84 (1H, m), 6.27 (2H, m), 6.96 (1H, d).

1. additionThe solution was poured into a separating funnel
2. customThe layers were separated
3. extractionthe aqueous layer extracted with ethyl acetate (3×10 ml)
4. washThe combined organic extracts were washed with brine (15 ml)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-159b80af589a4a5a945ad8a1181f212e

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933319B2