Propofol → 2-[2,6-Bis(isopropyl)phenoxycarbonyl]-benzoic Acid

HRID 2103785Notes

Reaction equation

HRID 2103785 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][CH:13]([C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([CH:22]([CH3:24])[CH3:23])[C:20]=1[OH:21])[CH3:14].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(OCC)C>[CH:22]([C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:13]([CH3:14])[CH3:12])[C:20]=1[O:21][C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[C:1]([OH:6])=[O:11])=[O:5])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 4943PropofolHCID 6811Phthalic AnhydrideHCID 8471Triethylamine

Product 1

HCID 211100142-[2,6-Bis(isopropyl)phenoxycarbonyl]-benzoic Acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of phthalic anhydride (0.84 g, 5.6 mmol) and propofol (1 g, 5.6 mmol) was added triethylamine (0.65 g, 6.4 mmol) and a catalytic amount of DMAP. The reaction mixture was brought to 90° C., stirred for 14 h, cooled to room temperature and diluted with ethyl ether (100 mL). The organic layer was washed with 10% aqueous citric acid solution (2×50 mL). The phases were separated and the organic phase was dried over MgSO4 and concentrated in vacuo. The crude product was sufficiently pure to be carried to the subsequent step.

Workup

  1. customwas brought to 90° C.
  2. washThe organic layer was washed with 10% aqueous citric acid solution (2×50 mL)
  3. customThe phases were separated
  4. dry with materialthe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95cb16d8660a4cf1999fe60471422bae
Source dataset
uspto-grants-2009_08
Patent number
US07576127B2

Reaction notes

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