Methane, dichloromethoxy- → 6-Hydroxy-1,3-dioxaindane-5-carbaldehyde

Temperature

0 °C

This Example was repeated on a larger scale. Sesamol (50.98 g, 369 mmol) was dissolved in 600 mL of CH2Cl2 followed by 52 mL (448 mmol) of SnCl4 and the solution was cooled to 0° C. Cl2CHOCH3 (35 mL, 387.5 mmol) was added dropwise as the reaction mixture warmed to room temperature, and was then stirred for 3 h. The mixture was poured over ice, the water layer was separated and extracted once with CH2Cl2 (30 mL). The organic extracts were combined, washed with 2M HCl (5×100 mL), and brine (50 mL), and then passed through a small column packed with MgSO4, which removed color. The solvent was evaporated to yield 28 g (46% yield): mp 119° C.; 1H-NMR (CDCl3) δ 9.63 (s, 1, CHO); 6.87 (s, 1, ArH); 6.47 (s, 1, ArH); 6.02 (s, 2, ArOCH2O); 1.54 (s, 1, ArOH); low resolution CIMS: m/z (rel. intensity) 167 (MH+, 100). Anal. Calcd. for C8H6O4: C, 57.84; H, 3.64. Found: C, 57.65; H, 3.76.

1. temperaturewarmed to room temperature
2. additionThe mixture was poured over ice
3. customthe water layer was separated
4. extractionextracted once with CH2Cl2 (30 mL)
5. washwashed with 2M HCl (5×100 mL), and brine (50 mL)
6. customremoved color
7. customThe solvent was evaporated
8. customto yield 28 g (46% yield)

ORD record

ord-6e9846d2b75a4aa0b3c621237d95252d

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318938B2