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

HRID 2408240

Reaction equation

HRID 2408240 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-cd845f9f9f244c17a0c39285d6b8c628
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Linked notes

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