反応 #83842

反応方程式

2.5-dimethylmandelic acid

ethyl oxomalonate

para-xylene

para-xylene

→

diethyl (2,5-dimethylphenyl)-hydroxymalonate

反応条件

後処理

1. 1
   workup.ADDITIONwas charged over 20 minutes
2. 2
   その他the mixture was quenched on a mixture of ice and 10M hydrochloric acid
3. 3
   抽出extracted into diethyl ether
4. 4
   洗浄The separated organic phase was washed with water
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   その他the solvent was evaporated under reduced pressure
8. 8
   workup.DISTILLATIONThe crude brown oil (31 parts) was then distilled under vacuum

実験手順

The method used to prepare 2.5-dimethylmandelic acid was similar to that described by Riebsomer and Irvine (Org.Synth.,Coll.Vol.3, p.327). Thus, ethyl oxomalonate (25 parts) in para-xylene (38 parts) was stirred at 0°-5° C. under a nitrogen atmosphere as anhydrous stannic chloride (46 parts) was charged over 20 minutes. The mixture was kept mobile by addition of further para-xylene (43 parts) and allowed to warm to ambient temperature. After 3 hours stirring, the mixture was quenched on a mixture of ice and 10M hydrochloric acid and extracted into diethyl ether. The separated organic phase was washed with water, dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude brown oil (31 parts) was then distilled under vacuum to give diethyl (2,5-dimethylphenyl)-hydroxymalonate (26 parts). 1Hnmr, 13Cnmr and mass spectra and micro-analysis were all consistent with the structure.

出典