Ozone → Benzenepropanal, .beta.-methyl-3-(1-methylethenyl)-

HRID 1165608Notes

Reaction equation

HRID 1165608 reaction equation
C(C1C=C(C(C)(C)C=O)C=CC=1)=CC.[CH:15]([CH2:17][CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]([CH3:30])[CH2:27]C=O)[CH:21]=1)[CH3:19])=[O:16].O=[O+][O-]>>[CH2:27]=[C:26]([C:22]1[CH:21]=[C:20]([CH:18]([CH3:19])[CH2:17][CH:15]=[O:16])[CH:25]=[CH:24][CH:23]=1)[CH3:30]

Participants

4

Reactant 3

HCID 24823OzoneHCID 19862292HCID 19862292, compoundHCID 53864984HCID 53864984, compound

Product 1

HCID 86208Benzenepropanal, .beta.-methyl-3-(1-methylethenyl)-

Procedure

m-Diisopropenylbenzene (237 g), 0.2 g butylated hydroxytoluene, 0.1 g NaHCO3, 0.0918 g RhHCO(PPh3)3 and 20 g triphenylphosphine were heated under a pressure of 250 psi hydrogen and 250 psi carbon monoxide at 110° C. for five hours and then at 140° C. for six hours. The crude reaction product was distilled to give 215 g of a liquid which analyzed as 49.4% starting material, 40.8% lb, 1.9% 2-(3-propen-ylphenyl)-2-methylpropanal and 4.9% 1,3-di-(1-formylpropan-2-yl)benzene. The constituents were readily separated by fractional distillation to give pure lb, b.p 98° C./0.1 mm Hg. The starting material may be recycled to give further product in an overall yield of 71.0% lb. IR and NMR spectra were compatible with the assigned structure. Odor: ozone, stemmy-green floral, melon. Odor value: 35,514; Odor threshold value: 0.7 ng/L.

Workup

  1. customThe constituents were readily separated by fractional distillation
  2. customto give pure lb, b.p 98° C./0.1 mm Hg
  3. customto give further product in an overall yield of 71.0% lb

Sources & evidence

ORD record
ord-9bf40f781ea94bc7acdf97e75a1646b6
Source dataset
uspto-grants-1990_03
Patent number
US04910346

Reaction notes

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