Electrolytic Phenylacetone 80%

bio · Working Bee

While perusing the following review article my eyes fell on this high yielding electrolytic oxidation rearrangement!

Would someone with JACS access please find the article
Corey, et al, JACS 82,2645, (1960). This should be real easy given the substrate is available without a major hassle.

Have not yet been able to find if benzyl hydroxyvaleric acid is available commercially or easily synthesized. Condensing Benzylalcohol or benzaldehyde with a valeric acid should be easy and hopefully high yielding. Given the price of phenylvaleric acid (ridiculous) the benzyl hydroxyvaleric is probably prohibitively expensive if available at all.

............................................................
ELECTROCHEMICAL OXIDATION OF ORGANIC COMPOUNDS
N. L. WEINBERG AND H. R. WEINBERG*
Central Research Division, American Cyanamid Company, Stamford, Connecticut 06904
Received February W6, 1968
Page 504 (g)' Rearrangement, Esterification, Halogenation

y-Benzyl- y-hydroxyvaleric acid substrate,
(CH3OH), (C2H5)3N) electrolyte

Carbon anode

Products:
Isopropyl benzyl ketone (5%), l-phenyl-2-methylbutan-3-
one (ll%), methyl benzyl ketone (80%), ethylene

ref (131) Corey, E. J., Bauld, N. L., LaLonde, R. T., Casanova, J.,
Jr., and Kaiser, E. T., J. Am. Chem. SOC., 82, 2645,(1960).

Here is some info of interest.

valeric acid.
(valerianic acid; n-pentanoic acid).
CAS: 109-52-4.
CH3(CH2)3COOH.
Properties: Colorless liquid; penetrating odor and taste. D 0.9394 (20/4C), bp 185.4C, refr index 1.4081 (20C), vap press 0.08 mm Hg (20C), fp ±34C, flash p 205F (96C) (OC). Soluble in water, alcohol and ether. Undergoes reactions typical of normal monobasic organic acids. Combustible.
Derivation: With other C5 acids by distillation from valerian, by oxidation of n-amyl alcohol, numerous essential oils.
Grade: Technical, reagent.
Hazard: Toxic by ingestion, strong irritant to skin and tissue.
Use: Intermediate for flavors and perfumes, ester-type lubricants, plasticizers, pharmaceuticals, vinyl stabilizers.

isovaleric acid.
(isopropylacetic acid).
CAS: 503-74-2.
(CH3)2CHCH2COOH.
Occurs in valerian, hop oil, tobacco, and other plants.
Properties: Colorless liquid; disagreeable taste and odor. D 0.931 (20/20C), bp 176C, refr index 1.4043 (20C), fp ±37C. Slightly soluble in water; soluble in alcohol and ether. Combustible.
Derivation: With other valeric acids, by distillation from valerian, by oxidation of isoamyl alcohol.
Use: Medicine, flavors, perfumes.

5-Phenylvaleric acid, 99%

Order Size Price Availability
5g 15.30 Back Order - Click for details.
25g 56.10 Back Order - Click for details.

CAS Number: 2270-20-4
Formula: C11H14O2
Formula Weight: 178.23
Form: White solid
Melting Point: 58-60°
Boiling Point: 176-178°/12mm

Any input on this idea is welcome and I will post more as I find it.
Definetly need the article as it should have a path to the benzylhydroxypentanoic acid substrate.