Water → 5-(1,1-Dimethyl-allyl)-2-hydroxy-benzaldehyde

Participants

Reaction Steps

A solution of boron trichloride (1M in CH2Cl2, 39.7 mmol) was added dropwise under argon at −78° C. to a stirred solution of 5-(1,1-Dimethyl-allyl)-2-methoxy-benzaldehyde (13.2 mmol) in dry CH2Cl2 (120 ml). The dry ice—acetone bath was removed and reaction allowed warming to RT. Stirred at RT for 18 hours, before the reaction mixture was cooled to 0° C. and iced water (125 ml) slowly added. Extracted with CH2Cl2 (2×100 ml). The organic phases were washed with brine, dried (Na2SO4), filtered, and evaporated to black oil. Purified by flash chromatography (heptane:EtOAc) to give the title product as yellow oil in 56% yield. 1H-NMR (CDCl3) δ 10.82 (s, 1H), 9.81 (s, 1H), 7.43 (d, 1H), 7.41 (s, 1H), 6.86 (d, 1H), 5.92 (dd, 1H), 5.02-4.96 (m, 2H), 1.34 (s, 6H).

Provenance & Evidence