# In Reimer-Tiemann reaction why does phenol attack the carbene from ortho position?

In step 5, why doesn't the oxygen attack the carbene. The way I see it: upon attacking the carbene from ortho position, the mechanism proceeds via a non aromatic intermediate. Oxygen bearing a negative charge is a good nucleophile too.

So I proceeded with oxygen acting as an nucleophile and came up with this mechanism:

The final product is not a major product (I wasn't even able to find it listed as a product after a cursory google search), so why does phenoxide attack the carbene from ortho position.

EDIT

• Jun 12, 2018 at 17:42
• Due to continuous conjugation of negative charge in phenoxide ion, the lone pair of electrons are present more at ortho position rather than at para position + carbene is highly electron deficient compound Jun 15, 2018 at 16:05

More over, attack from the ortho position, though creates a chance of Steric crowding, but the intermidiate generated from the attack by ortho-position creates an ordered transition state.The metal ion(say, $\ce{Na+}$) can easily interact with the electronegative $\ce{O}$ and $\ce{Cl}$ atoms, and can increase the stability of the transition state. Here is a picture of the intermidiate and a 3D view of it,
• what you have shown here needs a citation. Regardless I don't see why chlorine should have any interaction with the $\ce{Na+}$ ion. It doesn't have any charge on it. ("Backbonding" is not possible there is evidence that it forms a cyclopropyl dichloro ring) Jul 22, 2021 at 2:13
Another way of rationalising is through the use of the Hard-Soft Acid-Base principle. The dichlorocarbene generated is a soft electrophilic species while the oxyanion form of the phenoxide is a hard nucleophilic species. The nucleophilic $\pi$ bond is much softer and thus, it is much more favourable for it to be the attacking nucleophile (soft-soft interaction) rather than the negatively-charged oxygen atom (hard-soft interaction).