4-Hydroxybenzaldehyde → HCID 12419541, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 2.44 g (20 mmol; 1 eq.) of 4-hydroxybenzaldehyde are dissolved in 20 mL DMF, and 5.53 g (40 mmol; 2 eq.) of K2CO3 are added. After 1 hour's stirring at 70° C., the medium becomes pink. Using a dropping funnel, a solution of 2.4 mL (24 mmol; 1.2 eq.) of 4-bromobutyronitrile in 6 mL DMF are added slowly. The reaction medium is stirred 1 hour at 70° C. then 2 hours at 90° C. After cooling, the medium is filtered through a sintered glass filter. The filtrate is diluted with dichloromethane until precipitation, then filtered again through a sintered glass filter. The new filtrate is concentrated to dryness then re-dissolved in dichloromethane. The organic phase is washed twice in water then with a saturated NaCl solution, dried over Na2SO4 and concentrated to dryness. 4.15 g of compound (11) are obtained and used without any additional purification (quantitative yield).

Provenance & Evidence