Acetone → Propofol

HRID 543910Notes

Reaction equation

HRID 543910 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10]C(C)C)([CH3:3])[CH3:2].[CH3:14][C:15]([CH3:17])=O>>[CH:15]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:2])[CH3:3])[C:5]=1[OH:10])([CH3:17])[CH3:14]

Participants

3

Reactant 2

HCID 180AcetoneHCID 13531071Isopropyl 2-isopropylphenyl ether

Product 1

HCID 4943Propofol

Conditions

Temperature
150 °C

Procedure

To 15 g of isopropyl (2-isopropylphenyl) ether was added 8 g of 1% fluorided alumina. The mixture was placed in a 300 cc stirred autoclave and the system was flushed with nitrogen and left under a nitrogen atmosphere. The autoclave was heated to 150° C. for 1 hour with stirring during which time the pressure reached 200 psig. The cooled reaction mixture was taken up in acetone, filtered, and the solvent was removed on a rotary evaporator. The residue was analyzed by gas-liquid phase chromatography (glpc) which showed the presence of 2-isopropylphenol (10%), isopropyl(2-isopropylphenyl) ether (28%), 2,6-diisopropylphenol (60%), and 2,4,6-triisopropylphenol (2%). Thus, the 2,6-diisopropylphenol was formed with 83% selectivity.

Workup

  1. customthe system was flushed with nitrogen
  2. waitleft under a nitrogen atmosphere
  3. stirringwith stirring during which time the pressure
  4. customThe cooled reaction mixture
  5. filtrationfiltered
  6. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-266ccbe003434e5d8eb70f55371ba776
Source dataset
uspto-grants-1984_05
Patent number
US04447657

Reaction notes

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