Hydrochloric Acid → 3-(4-Methoxy-butyl)-benzaldehyde

Temperature

-72 °C

To a stirred solution of the title C compound, 1-bromo-3-(4-methoxy-butyl)-benzene (11 g, 45.24 mmol) in 200 mL of THF is added drop wise n-butyl lithium (31.1 mL, 49.76 mmol, 1.6 M solution in hexane) over 30 min at −72° C. The reaction mixture is further stirred 5 min at −72° C. before the addition of a THF solution (50 mL) of DMF (7.67 mL, 99.52 mmol) over 45 min. The reaction mixture is further stirred for 15 min at −72° C., 1 h at room and poured into aqueous 2 M HCl solution. The aqueous layer is extracted twice with ether and the combined organic extracts are dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash column chromatography on silica gel (hexane/EtOAc 9/1) to afford the title compound as a yellow oil: MS 210.0 [M+18]; Rt (HPLC, Nucleosil C18, 10:90-100:0 CH3CN/H2O+0.1% TFA within 5 min, then 100% CH3CN+0.1% TFA): 5.35 min.

1. extractionThe aqueous layer is extracted twice with ether
2. dry with materialthe combined organic extracts are dried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe residue is purified by flash column chromatography on silica gel (hexane/EtOAc 9/1)

ORD record

ord-552223e2df9040bd920ad4ea86cb29a2

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362040B2