Organic chemistry

Question

Does phenol react readily with formaldehyde in acidic or basic media? What are the products?

Answer 1

Phenol is a nucleophile, formaldehyde is a potent electrophile. Acid and base catalyzes this process. Since a protonated formaldehyde molecule is essentially a resonance stabilized carbocation (also known as oxocarbenium), it is therefore likely that it will undergo the Friedel-Crafts reaction (alkylation, not acylation).

This is actually a famous process...the first industrial scale polymer named  after the ”inventor” (first to patent this). This incredibly durable thermoset polymer is known as “Bakelite” and made it possible to create, for example, the original but now ancient landline telephones with rotary dials and a hangup button/stand.

Answer 2

Phenol readily reacts with Formaldehyde in Acid and Base to produce both the ortho and para substituted hydroxymethyl phenol products.  However without careful monitoring of conditions, both products can polymerize with other phenolic compounds to give high molecular weight polymers.