Sulfuric Acid → HCID 12480958, Verbindung

Temperatur

100 °C

Acidify a mixture of (2,2-dimethoxyethoxy)cyclohexane and water (30 mL) to a pH of 1.0 with sulfuric acid (9.0 M aqueous solution), and connect the mixture to a short-path distillation head. Reduce the pressure to 26.7 kPa and heat the mixture to 100° C. for 1 h. Cool the mixture to room temperature, then extract the aqueous layer with TBME (2×75 mL). Wash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL). Dry the organic phase over MgSO4, filter, and concentrate the filtrate under reduced pressure to furnish the title compound (634 mg, 51% yield). 1H NMR (400 MHz, CDCl3): δ 9.73 (t, J=1.0 Hz, 1H), 4.06 (d, J=1.0 Hz, 2H), 3.31 (tt, J=9.2, 3.9 Hz, 1H), 1.95-1.89 (m, 2H), 1.79-1.68 (m, 2H), 1.57-1.50 (m, 1H), 1.39-1.20 (m, 5H).

1. temperatureCool the mixture to room temperature
2. extractionextract the aqueous layer with TBME (2×75 mL)
3. washWash the combined organic layers with saturated aqueous NaHCO3 (75 mL) and saturated aqueous NaCl (75 mL)
4. dry with materialDry the organic phase over MgSO4
5. filtrationfilter
6. concentrationconcentrate the filtrate under reduced pressure

ORD-Eintrag

ord-0eb91556c55245a7a5c8526656c11fa4

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08962659B2