Propionic Acid → Methyl (4E)-4-methyl-5-(4-methylphenyl)-4-pentenoate

HRID 2408240

반응식

HRID 2408240 반응식
[C:1](OC)([O:5][CH3:6])([O:3]C)[CH3:2].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16](O)[C:17]([CH3:19])=[CH2:18])=[CH:12][CH:11]=1.C(O)(=O)CC>CO>[CH3:19]/[C:17](=[CH:16]\[C:13]1[CH:12]=[CH:11][C:10]([CH3:9])=[CH:15][CH:14]=1)/[CH2:18][CH2:2][C:1]([O:5][CH3:6])=[O:3]

참가 물질

5

반응물 3

HCID 1032Propionic AcidHCID 15050Trimethyl orthoacetateHCID 540233242-Methyl-1-(4-methylphenyl)prop-2-en-1-ol

생성물 1

HCID 58390609Methyl (4E)-4-methyl-5-(4-methylphenyl)-4-pentenoate수율 40.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Trimethyl orthoacetate (273 g, 2.24 mol) and 1-(4-methylphenyl)-2-methyl-2-propen-1-ol (91.4% pure, 39.92 g, 0.224 mol) were heated in the presence of propionic acid (0.5 ml) in an oil bath at 120°-150° C. The methanol formed during the reaction was distilled first, followed by the excess orthoacetate. The product was then freed from residual orthoacetate under vacuum and purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1), followed by bulb-to-bulb distillation (100° C./0.001 mbar). 19.62 g (yield=40%) of the desired product were obtained.

후처리

  1. distillationwas distilled first
  2. custompurified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 5:1)
  3. distillationfollowed by bulb-to-bulb distillation (100° C./0.001 mbar)

출처 및 근거

ORD 기록
ord-cd845f9f9f244c17a0c39285d6b8c628
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815792B2

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