Acetic Acid → 2,6-Diisopropylphenyl acetate

HRID 1441136Notes

Reaction equation

HRID 1441136 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[OH:13])([CH3:3])[CH3:2].[C:14](O)(=[O:16])[CH3:15]>FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>[C:14]([O:13][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:10]([CH3:12])[CH3:11])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 176Acetic Acid2×HCID 4943Propofol

Product 1

HCID 5960912,6-Diisopropylphenyl acetate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 9845Trifluoroacetic anhydrideSolvent

Procedure

A suspension of 2,6-diisopropylphenol (5.32 g) in 35 ml of trifluoroacetic anhydride is treated with 1.75 ml of glacial acetic acid under a nitrogen atmosphere. Upon completion of the addition of acetic acid, the solids are in mixture. Solvent evaporation gives an oil which is taken up in 150 ml of ethyl acetate and washed twice with saturated aqueous sodium bicarbonate and once with saline. Drying of the organic layer with sodium sulfate followed by filtration and solvent evaporation gives 6.55 g of an oil which is chromatographed on 330 g of silica gel eluting with chloroform/hexane (9/1). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3, TMS) 7.2, 2.91, 2.36, 1.20.

Workup

  1. customSolvent evaporation
  2. customgives an oil which
  3. washwashed twice with saturated aqueous sodium bicarbonate and once with saline
  4. dry with materialDrying of the organic layer with sodium sulfate
  5. filtrationfollowed by filtration and solvent evaporation

Sources & evidence

ORD record
ord-47a25cf48a2a45d784aaad5f48237b27
Source dataset
uspto-grants-1996_03
Patent number
US05502187

Reaction notes

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