4-tert-Butyl-2,6-diformylphenol

Uses

1. Used as a key intermediate for the production of a BODIPY chemodosimetric sensor for cyanide ions. 2. Used as a key intermediate for a Pro-ligand in bimetallic catalysis.

General Description

4-tert-Butyl-2,6-diformylphenol can be prepared from 4-tert-butylphenol and hexamethylenetetramine.

Synthesis

The general procedure for the synthesis of 4-tert-butyl-2,6-formylphenol from (5-(tert-butyl)-2-hydroxy-1,3-phenyl)dimethanol was as follows: activated MnO2 (40 g) was added to CHCl3 (200 mL) in a 500 mL round-bottom flask. The mixture was heated under stirring to reflux for about 15 minutes, then powder of (5-(tert-butyl)-2-hydroxy-1,3-phenyl)dimethanol (5.0 g) was added slowly. After keeping the reaction at reflux for 8 hours, the reaction mixture was cooled to room temperature and filtered through a Brinell funnel. The solid residue was washed thoroughly with CHCl3 (40 mL x 5) until the filtrate was colorless. The filtrates were combined and concentrated using a rotary evaporator to give the yellow solid product 4-tert-butyl-2,6-formylphenol (3.8 g, 77% yield).

References

[1] Synthetic Communications, 2000, vol. 30, # 9, p. 1555 - 1561
[2] Tetrahedron Letters, 2012, vol. 53, # 7, p. 804 - 807
[3] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 9, p. 2683 - 2684
[4] Chemische Berichte, 1994, vol. 127, # 3, p. 465 - 476
[5] Chemische Berichte, 1942, vol. 75, p. 363,366