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

HRID 2408240

反応式

HRID 2408240 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cd845f9f9f244c17a0c39285d6b8c628
出典データセット
uspto-grants-2014_08
特許番号
US08815792B2

関連ノート

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