4-(4-formylphenoxy)butanenitrile

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). The reaction medium is stirred 1 hour at 70° C. 2 hours at 90° C After cooling the medium is filtered through a sintered glass filter The filtrate is diluted with dichloromethane until precipitation 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 with a saturated NaCl solution, dried over Na2SO4 concentrated to dryness

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). The reaction medium is stirred 1 hour at 70° C. 2 hours at 90° C After cooling the medium is filtered through a sintered glass filter The filtrate is diluted with dichloromethane until precipitation 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 with a saturated NaCl solution, dried over Na2SO4 concentrated to dryness

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Hydroxybenzaldehyde (20 mmol) was dissolved in absolute EtOH (150 mL) and treated with solid NaOEt (24 mmol). After stirring for 15 minutes, 4-bromobutyronitrile (24 mmol) was added and reaction mixture was heated overnight at 90° C. in an oil bath. After letting the reaction cool to room temperature, volatiles were removed, the residue was taken up in ice, adjusted to pH 6 with 1N sulfuric acid, and extracted with methylene chloride. The organic phase was washed with brine, dried over MgSO4 and concentrated. Chromatography over silica gel (eluant, 5% EtOAc in hexanes) gave the 4-(3-cyanopropoxy)benzaldehyde (4.8 g, 58%). reaction mixture cool to room temperature volatiles were removed extracted with methylene chloride The organic phase was washed with brine dried over MgSO4 concentrated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). The reaction medium is stirred 1 hour at 70° C. 2 hours at 90° C After cooling the medium is filtered through a sintered glass filter The filtrate is diluted with dichloromethane until precipitation 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 with a saturated NaCl solution, dried over Na2SO4 concentrated to dryness