Pyridine → 2,2-Dimethylpropanoic acid, 4-hydroxy-2,3,6-trimethylphenyl ester
Reaction equation
[CH3:1][C:2]1[C:3]([OH:11])=[C:4]([CH3:10])[C:5]([CH3:9])=[C:6]([CH:8]=1)[OH:7].N1C=CC=CC=1.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[CH3:20][C:19]([CH3:22])([CH3:21])[C:18]([O:11][C:3]1[C:2]([CH3:1])=[CH:8][C:6]([OH:7])=[C:5]([CH3:9])[C:4]=1[CH3:10])=[O:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A 500 mL round bottom flask is equipped with a stirring bar and charged with 15.2 g (100 mmol) of trimethylhydroquinone and 23.7 g (3×100 mmol) of pyridine in 100 mL dichloromethane. The solution is stirred at ambient temperature and a solution of 20.8 g (100 mmol) of pivaloyl chloride in 100 mL of dichloromethane is added over 15 minutes. The final solution is stirred at ambient temperature for 48 hours, then washed with 1×100 mL of 3N hydrochloric acid solution, 1×50 mL of 3N hydrochloric acid solution, water, dried (magnesium sulfate) and evaporated leaving 26.6 g (>100%) of a pale yellow solid, mp 88°-112° C. (after drying 24.1 g). Recrystallization from hexane in the presence of charcoal affords the title compound as colorless cubes; mp 119°-121° C.
Workup
- customA 500 mL round bottom flask is equipped with a stirring bar
- washwashed with 1×100 mL of 3N hydrochloric acid solution, 1×50 mL of 3N hydrochloric acid solution, water
- dry with materialdried (magnesium sulfate)
- customevaporated
- customleaving
- dry with material26.6 g (>100%) of a pale yellow solid, mp 88°-112° C. (after drying 24.1 g)
- customRecrystallization from hexane in the presence of charcoal
Sources & evidence
- ORD record
- ord-114e79d047764dc2b549f7d56a5d8b8d
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05166398
Reaction notes
Loading…