Hydrochloric Acid → Triethyl orthoacetate

온도

-10 °C

410 g (10 moles) of acetonitrile and 483 g (10.5 moles) of ethanol are dissolved in 900 g of decaline and the mixture is cooled to -10° C. With stirring, 383 g (10.5 moles) of anhydrous hydrogen chloride is introduced directly into the solution. The HCl introduction period amounts to 80 minutes, the temperature increasing, despite continued refrigeration, to +7° C. After completion of the HCl introduction, the temperature is raised to 30° C.; after 2.5 hours the imidoethyl ester hydrochloride crystallizes out; then stirring is continued at 30° C. for another 11 hours. 1150 grams of ethanol (25 moles) is then added to the solution and it is neutralized against methyl red with 115 g of a 20% solution of sodium ethylate in ethanol. After the neutralization, the temperature is raised to 35° C. and the mixture is stirred for 5 hours. After it has been chilled to 10° C., the ammonium chloride is centrifuged out and washed with decaline. The combined filtrates are treated, after chloride determination (titration with AgNO3), with an appropriate excess of sodium ethanolate (35 g of 20% solution of sodium ethanolate in ethanol). The filtrate thus treated is distilled in vacuo in a packed column. 1414 g of triethyl orthoacetate (B.P. 66°-68° C. at 41 Torr) is obtained (8.73 moles= 87.3% with respect to acetonitrile input and 91.2% with respect to reacted acetonitrile). After the acetamide has been filtered out of the sump phase, the decaline thus purified can be reused.

1. temperaturethe temperature increasing
2. customto +7° C
3. customafter 2.5 hours the imidoethyl ester hydrochloride crystallizes out
4. stirringthen stirring
5. temperatureAfter the neutralization, the temperature is raised to 35° C.
6. stirringthe mixture is stirred for 5 hours
7. temperatureAfter it has been chilled to 10° C.
8. washwashed with decaline
9. additionThe combined filtrates are treated
10. additionThe filtrate thus treated
11. distillationis distilled in vacuo in a packed column

ORD 기록

ord-ca5f18843d254c93bc561ae220eafb09

출처 데이터셋

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04182910