Trifluoroacetic anhydride → HCID 20484725, compound

HRID 1808724Notes

Reaction equation

HRID 1808724 reaction equation
[CH3:1][CH:2]1[CH:7]([CH3:8])[CH:6]([CH3:9])[CH2:5][CH:4]([OH:10])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>ClCCl.C(OCC)C>[CH3:1][CH:2]1[CH:7]([CH3:8])[CH:6]([CH3:9])[CH2:5][C:4](=[O:10])[CH2:3]1

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 138620913,4,5-Trimethylcyclohexanol

Product 1

HCID 20484725HCID 20484725, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

3,4,5-trimethylcyclohexanol obtained in step 1 was dissolved in dichloromethane. Dess-Martin reagent (3.1 g, 7.34 mmol) was added in one portion. Trifluoroacetic acid anhydride (0.56 mL, 7.34 mmol) was added, and the solution was stirred at RT for 18 h. Sodium hydroxide (1 N, 30 mL) and diethyl ether (100 mL) were added. The reaction mixture was stirred at RT for one hour. The organic layer was washed with NaOH (1N, 30 ml), brine 930 ml), dried over anhydrous Na2SO4, filtered, and concentrated. The product was purified by SiO2 chromatography (Hexane/EtOAc 5:1) to give 3,4,5-trimethylcyclohexanone (758 mg, 73.6% from 3,4,5-trimethylphenol).

Workup

  1. stirringThe reaction mixture was stirred at RT for one hour
  2. washThe organic layer was washed with NaOH (1N, 30 ml), brine 930 ml),
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by SiO2 chromatography (Hexane/EtOAc 5:1)

Sources & evidence

ORD record
ord-09fc65bddd46452397b54d19fbe52911
Source dataset
uspto-grants-2013_01
Patent number
US08361959B2

Reaction notes

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