复旦大学：《有机化学实验 Organic chemistry lab》课程教学资源（实验讲义）The synthesis of DBA

E Organic chemistry experiment The synthesis of DBa Experimental center of chemical education Fudan University

The synthesis of DBA Experimental center of chemical education Fudan University Organic chemistry experiment

Target 1. Master the principle of aldol reaction 2. Obtain the product through controlling the ratio of starting materials

1.Master the principle of aldol reaction. 2.Obtain the product through controlling the ratio of starting materials. Target

Background Pd,( dba)3 is a good source of pd(o) which is widely used as a catalyst in cross coupling -Pd ---Pd

Pd2 (dba)3 is a good source of Pd(0) which is widely used as a catalyst in cross coupling. Background

迫 Experimental principle 1.Two molecule of carbonyl compounds with a-H. can condense to form B-hydroxy aldehyde(ketone). While rasing the reaction temperature, will form further form a, B unsaturated aldehyde(ketone) 2. A non-aH aromatic aldehyde can condense with carbonyl compounds containing a-h to form o, B-unsaturated aldehyde (ketone), it is so-called Clasien-Schmidt reaction

1.Two molecule of carbonyl compounds with α-H, can condense to form β-hydroxy aldehyde(ketone). While rasing the reaction temperature, will form further form α,β- unsaturated aldehyde (ketone). 2. A non- α-H aromatic aldehyde can condense with carbonyl compounds containing α-H to form α,β-unsaturated aldehyde (ketone), it is so-called Clasien-Schmidt reaction. Experimental principle

NIV 迫 Experimental principle H2O OH O

Experimental principle

迫套 Reagents M p b p Benzaldehyde 106.12 -26 179 041 Acetone 58.08 95 56 1.359 EtOH 46.07 114 78 0.789 DBA 234.3 13 130(27Pa)

Benzaldehyde 106.12 -26 179 1.041 Acetone 58.08 -95 56 1.359 EtOH 46.07 -114 78 0.789 DBA 234.3 113 130(2.7Pa) Reagents M.w. m.p. b.p. d

The synthesis of DBA ynthesis 2.0 g NaOH, 20 mL H,O, cool down 16 mL EtoH added to 100 mL three-neck flask water bath RB2. 2.1 g PhCHO, 0.58 g Acetone mixed slowly added half to flask control the temperature 3. 15 min added the rest. etoh washed 4. 30 min later suction filtration, washed by H,O, dry, weigh Recrystalization Crude product is added to 50 mL round-bottomed flask EtOh is added(about 5 mL/g) 2. Water bath, reflux, EtoH is added slowly until totally dissolved 3. Cool down to r t, followed by icy water bath 4. Suction filtration, washed by H,O, dry, weigh

1. 2.0 g NaOH， 20 mL H2O，cool down 16 mL EtOH added to 100 mL three-neck flask water bath 2. 2.1 g PhCHO， 0.58 g Acetone mixed slowly added half to flask control the temperature 3. 15 min added the rest， EtOH washed 4. 30 min later suction filtration , washed by H2O, dry, weigh 1. Crude product is added to 50 mL round-bottomed flask EtOH is added (about 5 mL/g ) 2. Water bath, reflux, EtOH is added slowly until totally dissolved 3. Cool down to r.t., followed by icy water bath 4. Suction filtration, washed by H2O, dry, weigh Synthesis Recrystalization The synthesis of DBA

Attention 1. Stir should be kept during reaction to ensure sufficient reaction 2. PhCHO and acetone should be weighed exactly

1. Stir should be kept during reaction to ensure sufficient reaction. 2. PhCHO and acetone should be weighed exactly. Attention