تفاعل #415972

معادلة التفاعل

bromoacetaldehyde diethylacetal

sodium hydride

p-fluorophenol

hexane

→

desired product

المردود 82.0%

4-fluorophenoxyacetaldehyde diethylacetal

المردود 82.0%

المذيبات

dimethylformamide

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةfinally heated on a steam bath for 4 hours
2. 2
   أخرىto come to room temperature
3. 3
   ترشيحthe precipitated sodium bromide is filtered off
4. 4
   أخرىDimethylformamide is then removed on a rotary evaporator
5. 5
   workup.ADDITIONthe oil residue is diluted with acetone (100 ml.)
6. 6
   أخرىanother quantity of sodium bromide is precipitated which
7. 7
   أخرىagain is removed by filtration
8. 8
   تركيزThe filtrate is then concentrated on a rotary evaporator
9. 9
   أخرىleaving an oil residue which
10. 10
    workup.DISTILLATIONdistilled at 87° C./0.05 mm

الإجراء التجريبي

A solution of p-fluorophenol (28.1 g., 0.25 mole) in dimethylformamide (30 ml.) is added dropwise to a suspension of hexane (2 × 30 ml.)-prewashed sodium hydride (50% oil dispersion, 12.5 g., 0.26 mole) in dimethylformamide (120 ml.). The resulting mixture is stirred at room temperature for 10 minutes, treated with bromoacetaldehyde diethylacetal (49.3 g., 0.25 mole), and finally heated on a steam bath for 4 hours. The reaction mixture is allowed to come to room temperature and the precipitated sodium bromide is filtered off. Dimethylformamide is then removed on a rotary evaporator, the oil residue is diluted with acetone (100 ml.) and another quantity of sodium bromide is precipitated which again is removed by filtration. The filtrate is then concentrated on a rotary evaporator leaving an oil residue which is vacuum distilled at 87° C./0.05 mm. to yield the desired product as colorless oil (46.7 g., 0.205 mole, 82%). ir (neat) 3.4~3.5, 6.21, 6.64, 8.00, 8.25, 8.83, 9.32, 12.08, 13.20μ; pmr (CCl4)δ1.17 (6H, t, J=7.5Hz), 3.57 (2H, q, J=7.5Hz), 3.61 (2H, q, J=7.5Hz), 3.85 (2H, d, J=5Hz), 4.68 (1H, t, J=5Hz), 6.6-7.1 (4H, m).

المصدر