3-Hydroxybenzaldehyde → HCID 11416458, compound

Participants

Reaction Conditions

Reaction Steps

99.0 g (663 mmol) of 4-tert-butylaniline was dissolved in 500 ml of acetonitrile, and 51.6 ml (670 mmol) of trifluoroacetic acid was added with ice-cooling. 46.4 g (670 mmol) of 3,4-dihydro-2H-pyran and 81.8 g (670 mmol) of 3-hydroxybenzaldehyde in 500 ml of acetonitrile were initially introduced in a second flask with ice-cooling. The aniline*|trifluoroacetic acid salt pre-cooled to 50° C. was added rapidly to this reaction solution, and stirring was continued at this temperature for about 2 h. The reaction mixture was evaporated, and the residue was suspended in 2 l of water and adjusted to pH 12 using sodium hydroxide solution. The emulsion formed was extracted 2× with 1 l of tert-butyl methyl ether. The org. phase was dried over Na2SO4 and crystallised overnight in at 4° C. Precipitated colourless product 1 was filtered off and dried, giving 6.00 of colourless crystals. 3-(9-tert-Butyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-5-yl)phenol was isolated from the filtrate as described under DE10360154.6 and could also be converted into comp. 1 as described under c.

Provenance & Evidence