Reaction #1470439

Reaction equation

Succinic anhydride

2,6-diisopropylphenol

→

2,6-diisopropylphenyl hydrogen succinate

Yield 80.2%

Solvents

triethylamine

Conditions

Workup

1. 1
   Othersolvents were removed under vacuum
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water
3. 3
   workup.ADDITIONadded to an iced solution of dilute hydrochloric acid
4. 4
   FiltrationThe precipitated product was filtered
5. 5
   Otherrecrystallized from ethanol-water

Procedure

Succinic anhydride (14 g, 140 mmol) and dimethylaminopyridine (0.02 g, 0.16 mmol) were added to a solution of 2,6-diisopropylphenol (20.8 ml, 112 mmol) in triethylamine (50 ml) under nitrogen. After 16 hr at room temperature, solvents were removed under vacuum. The residue was dissolved in water and added to an iced solution of dilute hydrochloric acid. The precipitated product was filtered and recrystallized from ethanol-water to yield 25.0 g (80.2% yield) of 2,6-diisopropylphenyl hydrogen succinate (propofol hemisuccinate), mp 101-102° C.

Source