Acetic Acid → 2,6-Diisopropylphenyl acetate

HRID 2065981

Reaction equation

HRID 2065981 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([OH:17])(=[O:16])[CH3:15].[CH:18]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([CH3:29])[CH3:28])[C:22]=1O)([CH3:20])[CH3:19]>O>[C:14]([O:17][C:22]1[C:21]([CH:18]([CH3:19])[CH3:20])=[CH:26][CH:25]=[CH:24][C:23]=1[CH:27]([CH3:29])[CH3:28])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4943PropofolHCID 9845Trifluoroacetic anhydride

Product 1

HCID 5960912,6-Diisopropylphenyl acetateYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

3.45 g (16.4 mmol) of trifluoroacetic anhydride is added to 0.83 ml (14.6 mmol) of acetic acid at 0° C. while leaving the mixture to return to ambient temperature over 2 hours. The mixture is then cooled down to 0° C. and 1.95 g (11.0 mmol) of 2,6-diisopropylphenol is added dropwise. The reaction medium is maintained under stirring for 12 hours before being poured into ice-cooled water. After extraction with dichloromethane, the organic phase is washed with sodium chloride in a saturated aqueous solution before being dried over magnesium sulphate, filtered and concentrated under vacuum. A colourless oil is obtained with a yield of 86%. This product is sufficiently pure to be used directly in the following stage.

Workup

  1. customwhile leaving the mixture
  2. temperatureThe reaction medium is maintained
  3. additionbefore being poured into ice-
  4. extractionAfter extraction with dichloromethane
  5. washthe organic phase is washed with sodium chloride in a saturated aqueous solution
  6. dry with materialbefore being dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customA colourless oil is obtained with a yield of 86%

Sources & evidence

ORD record
ord-c9ac66a01b0045e497c52de8b4afe73e
Source dataset
uspto-grants-2012_10
Patent number
US08288560B2

Linked notes

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