Propofol → 184869-48-5

HRID 279246Notes

Reaction equation

HRID 279246 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[C:12]=1[OH:20])([CH3:10])[CH3:9]>C(N(CC)CC)C.CN(C1C=CC=CN=1)C>[C:4]([O:20][C:12]1[C:13]([CH:17]([CH3:18])[CH3:19])=[CH:14][CH:15]=[CH:16][C:11]=1[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7]

Participants

5

Reactant 2

HCID 4943PropofolHCID 7922Succinic anhydride

Product 1

HCID 9925625184869-48-5Yield 80.2%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 8471TriethylamineSolvent

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.

Workup

  1. customsolvents were removed under vacuum
  2. dissolutionThe residue was dissolved in water
  3. additionadded to an iced solution of dilute hydrochloric acid
  4. filtrationThe precipitated product was filtered
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-47a5688104034967ba470dc582fb3ab5
Source dataset
uspto-grants-2002_03
Patent number
US06362234B1

Reaction notes

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