Styrene --> P2P?

[Rhodium]

Palladium Catalyzed, Regioselective Reduction of 1,2-Epoxides by Ammonium Formate
Peter S. Dragovich, Thomas J. Prins, Ru Zhou

J. Org. Chem. 60, 4922-4924 (1995)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/cth.epoxides.pdf)
____ ___ __ _

The Reactions of Monomeric Styrenes
William S. Everson

Chem. Rev. 45, 183-345 (1949)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/styrene.rxn.review.pdf) (8 MB)

[methymouse]

There is apparently an enormous body of literature concerning the conversion of acetylene to acetaldehyde, notably the use of a mercury(II) salt, which reacts with the acetylene, and is then hydrolized to acetaldehyde.  I wonder of the same technique could be applied to the manufacture of phenylacetaldehyde from styrene.  Patent

Patent GB312716

is especially interesting, since it lists the possibility of using sodium bisulfate and a Cu(II) salt--forgoing the mercury.  See

Post 435662

(lugh: "From Acetylene", Novel Discourse)

Styrocrank may yet be a reality.

So far the most promising routes seem to be the reduction of styrene epoxide to beta-phenethyl alcohol with Pd/C and NH4COO, the Pinacol rearrangement of the 1,2-diol with H2SO4, and this.

Edit:  Man do I feel like a jackass.  Acetylene is C2H2.  Lousy nomenclature...  Grumble grumble.

[roger2003]

Found in wanted references:

Improved synthesis of phenylacetamides by the Willgerodt reaction with microwave heating.
Strauss, Christopher R.; Trainor, Robert W.
Organic Preparations and Procedures International (1995),  27(5), 552-5.

http://hyperlab.0catch.com/OPPI_1995_27_552.djvu

[lugh]

High-yield synthesis from styrene oxide or styrene glycol:  G. Paparatto, G. Gregorio, Tetrahedron Letters 29, 1471 (1988)

https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000486303-papparatto.djvu" target="_blank" title="Download this file">

[roger2003]

This compound is used in the converting-process:

P-Tert-Butylcatechol(TBC)

Synonyms 4-Tert-Butyl Catechol,4-tert-Butylpyrocatechol
CAS Number:98-29-3

Appearance: white or pale yellow Flake
Assay:99.5%
Melting Point:53
Crystal Point:52
Boiling Point:285
Ash:0.13%
Packing:30kg Drum

4-Tert-Butyl Catechol is mainly employed in the distillation and transportation of olefin monomer as high efficient retarder. 4-Tert-Butyl Catechol especially suits styrene, butadiene, chloroprene, and chloroethylene . 4-Tert-Butyl Catechol?can also be used as antioxidant of polythene, polypropylene, nylon and other polymers, oil and its ramifications,ethyl cellulose lacquer, lubricants, and metallic soap,etc. Besides, it can serve as passivating agent of the catalyst of carbamater and stabilizer of various kinds of organic compounds.