[mghis]

Hello,

I am wondering how to synthesize this compound, used a few decades ago for developing film.

"The Merck Index" says it is produced with chloroacetic acid and p-aminophenol with the following reaction:
Cl-CH₂-COOH + HO-C₆H₄-NH₂ C₈H₉NO₃ + HCl

I also thought I could use glycine and p-chlorophenol, with the reaction:
NH₂-CH₂-COOH + Cl-C₆H₄-OH C₈H₉NO₃ + HCl

Would these reaction work? Are they spontaneous reactions? Do I need a catalizer, or maybe some particular pH to get them started? Can you suggest me a suitable solvent and a way to separate my product?

In short, I need a recipe, some pratical suggestion.

Thanks for any answer, and sorry for my poor English.

     -- mghis

[sjb]

Hello,

I am wondering how to synthesize this compound, used a few decades ago for developing film.

"The Merck Index" says it is produced with chloroacetic acid and p-aminophenol with the following reaction:
Cl-CH₂-COOH + HO-C₆H₄-NH₂ C₈H₉NO₃ + HCl

I also thought I could use glycine and p-chlorophenol, with the reaction:
NH₂-CH₂-COOH + Cl-C₆H₄-OH C₈H₉NO₃ + HCl

Would these reaction work? Are they spontaneous reactions? Do I need a catalizer, or maybe some particular pH to get them started? Can you suggest me a suitable solvent and a way to separate my product?

In short, I need a recipe, some pratical suggestion.

Thanks for any answer, and sorry for my poor English.

     -- mghis

Several problems I can think of. What's the mechanism of displacement at your aryl chloride? Are there any other reactive sites?

[mghis]

Several problems I can think of. What's the mechanism of displacement at your aryl chloride? Are there any other reactive sites?

Well, maybe using an aryl chloride wasn't such a good idea. 
I was hoping that the hydroxyl at p- would somewhat work as activating group, like -NO₂, to allow nucleophilic displacement of Cl.

Fine, let's put aside p-chlorophenol and glycine. What about the first reaction? (the one using p-amminophenol and chloroacetic acid)

[sjb]

I think the Merck index may have references (or at least it used to, a while back). Failing that, anything on the wiki page of help, or in things like Scifinder or Crossfire?

[mghis]

I think the Merck index may have references (or at least it used to, a while back). Failing that, anything on the wiki page of help, or in things like Scifinder or Crossfire?

The Merck Index has indeed a few references: "Vater, J. Prakt. Chem. 29, 291 (1884); Meldola et al., J. Chem. Soc. 111, 552 (1917); Galatis, Helv. Chim. Acta 4, 576 (1921)."  I have found them on the on-line archive of their journals. Their titles are "Ueber die Einwirkung der Monochloressigsäure auf Ortho- und Paraamidophenol und die sich hierdurch bildenden Oxyphenylglycine", "Attempts to prepare asymmetric quinqueralent nitrogen compounds. Part III. Hydroxyphenylglycine", and "Sur quelques dérivés de la p-oxyphényle-glycine".

They seem very useful, but unfortunately I cannot read them, since I am not a subscriber of those journals.  I cannot either search the archives you told me about, unless I subscribe and pay a considerable fee.

Thanks again for your help.