Propionic Acid → HCID 67330102, compound

HRID 2408243Notes

Reaction equation

HRID 2408243 reaction equation
[C:1](OC)([O:5][CH3:6])([O:3]C)[CH3:2].[C:9]1([CH:15](O)[C:16]([CH3:18])=[CH2:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(=O)CC>CO>[CH3:17]/[C:16](=[CH:15]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[CH2:18][CH2:2][C:1]([O:5][CH3:6])=[O:3]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 15050Trimethyl orthoacetateHCID 1382112-Methyl-1-phenylprop-2-en-1-ol

Product 1

HCID 67330102HCID 67330102, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trimethyl orthoacetate (186 g, 1.52 mol) and 1-phenyl-2-methyl-2-propen-1-ol (90% pure from Alfa Aesar, 25 g, 0.152 mol) were heated in the presence of propionic acid (0.2 ml) in an oil bath at 145° C. for 4 hours. The methanol formed during the reaction was distilled. The excess orthoacetate was then removed under vacuum and the residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 8:1) followed by bulb-to-bulb distillation (67° C./0.001 mbar). 6.5 g (yield=21%) of the desired product were obtained.

Workup

  1. distillationwas distilled
  2. customThe excess orthoacetate was then removed under vacuum
  3. customthe residue was purified by column chromatography on silica gel (eluent: heptanes/ethyl acetate 25:1 to 8:1)
  4. distillationfollowed by bulb-to-bulb distillation (67° C./0.001 mbar)

Sources & evidence

ORD record
ord-d30270d395fc49209f089ff6d6301b15
Source dataset
uspto-grants-2014_08
Patent number
US08815792B2

Reaction notes

Loading…