Methane, dichloromethoxy- → HCID 23532365, compound

Temperature

0 °C

Into a 100-mL round-bottom flask, was placed a solution of 2,3-dihydro-1H-inden-4-ol (3.0 g, 22.36 mmol, 1.00 equiv) in dichloromethane (20 ml) and TiCl4 (7.66 g, 40.38 mmol, 1.80 equiv). After 5 minutes, dichloro(methoxy)methane (2.81 g, 24.44 mmol, 1.10 equiv) was added at 0° C. in a water/ice bath and the resulting solution stirred for 3 h at 0° C. The reaction was then quenched by the addition of 25 mL of water. The resulting solution was extracted with 2×150 mL of dichloromethane. The organic layers were combined, washed with 1×50 mL of H2O, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1:2.3). This resulted in 1.26 g (35%) of 7-hydroxy-2,3-dihydro-1H-indene-4-carbaldehyde as a light yellow solid. Mass spectrum (ESI, m/z): Calcd. for C10H10O2, 163.1 (M+H). found 163.1.

1. customInto a 100-mL round-bottom flask, was placed
2. customThe reaction was then quenched by the addition of 25 mL of water
3. extractionThe resulting solution was extracted with 2×150 mL of dichloromethane
4. washwashed with 1×50 mL of H2O
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. washeluted with ethyl acetate/petroleum ether (1:2.3)
8. customThis resulted in 1.26 g (35%) of 7-hydroxy-2,3-dihydro-1H-indene-4-carbaldehyde as a light yellow solid

ORD record

ord-8a54ca932737467ca6eda7b1ae5090b1

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1