تفاعل #47557

معادلة التفاعل

3-chloro-but-2-enoic acid ethyl ester

Potassium t-butoxide

3-methyl-phenol

→

(E)-3-m-tolyloxy-but-2-enoic acid ethyl ester

المردود 63.3%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated
2. 2
   درجة الحرارةto reflux for 0.75 h
3. 3
   درجة الحرارةThe reaction mixture was refluxed for an additional 3 h
4. 4
   تركيزAfter this time, the mixture was concentrated in vacuo
5. 5
   workup.ADDITIONthe residue was diluted with water
6. 6
   استخلاصextracted with diethyl ether
7. 7
   غسيلThe organic layer was then washed with 5% aqueous sodium hydroxide solution
8. 8
   تجفيفdried over sodium sulfate
9. 9
   تركيزconcentrated in vacuo

الإجراء التجريبي

Potassium t-butoxide (10.4 g, 0.092 mol) was added to a stirred solution of 3-methyl-phenol (5.00 g, 0.046 mol) in tetrahydrofuran (35 mL) at 23° C. under nitrogen and the reaction mixture was heated to reflux for 0.75 h. The reaction mixture was cooled to 23° C. and a solution of 3-chloro-but-2-enoic acid ethyl ester (prepared as in Example 191, 6.85 g, 0.046 mol) in tetrahydrofuran (40 mL) was added to the reaction mixture. The reaction mixture was refluxed for an additional 3 h. After this time, the mixture was concentrated in vacuo and the residue was diluted with water and extracted with diethyl ether. The organic layer was then washed with 5% aqueous sodium hydroxide solution followed by a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to afford (E)-3-m-tolyloxy-but-2-enoic acid ethyl ester (6.41 g, 63%) as a yellow oil.

المصدر