Reaction #5647

Reaction equation

diester

4-(2-methoxy-4-benzyloxyphenyl)pyridine-2,6-dicarboxylic acid dimethyl ester

→

phenol

Yield 89.0%

4-(2-methoxy-4-hydroxyphenyl)pyridine 2,6-dicarboxylic acid dimethyl ester

Yield 89.0%

Solvents

ethanol

Conditions

Workup

1. 1
   OtherThe container for the resulting suspension was evacuated
2. 2
   workup.ADDITIONfilled with H2 (repeated three times)
3. 3
   workup.ADDITIONfilled rubber bladder for 60 hours with very rapid stirring
4. 4
   FiltrationThe mixture was then filtered
5. 5
   Otherto remove catalyst
6. 6
   Otherthe solvent was removed from the filtrate by rotary evaporation
7. 7
   OtherThe resulting oil was dried in vacuo

Procedure

To a solution of 7 g (0.174 mole) of the diester 23 in 200 ml of ethanol was added 1.0 g of 10% Pd/C. The container for the resulting suspension was evacuated and filled with H2 (repeated three times) and kept under a positive atomosphere by means of a hydrogen-filled rubber bladder for 60 hours with very rapid stirring. The mixture was then filtered to remove catalyst and the solvent was removed from the filtrate by rotary evaporation. The resulting oil was dried in vacuo yielding after several hours (4.9 g) 89% of the desired phenol 24 as a solid.

Source