Sodium Iodide → Benzyl 4-(2,2,2-trifluoroethoxy)phenyl ketone

HRID 477435Notes

Reaction equation

HRID 477435 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].C1(C)C=CC(S(O[CH2:35][C:36]([F:39])([F:38])[F:37])(=O)=O)=CC=1>CN(C)C=O.CS(C)=O>[F:37][C:36]([F:39])([F:38])[CH2:35][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:9])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 75607Benzyl 4-hydroxyphenyl ketone

Product 1

HCID 13881621Benzyl 4-(2,2,2-trifluoroethoxy)phenyl ketone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of benzyl 4-hydroxyphenyl ketone (12.5 g; 0.059 mol), potassium carbonate (11.2 g; 0.08 mol) and sodium iodide (0.5 g) in dimethylformamide (80 ml) was heated to 130° C. At this temperature, 2,2,2-trifluoroethyl p-toluenesulphonate (16.4 g; 0.066 mol), dissolved in dimethyl sulphoxide (30 ml), was added dropwise over 30 minutes. It was then stirred for 45 minutes at a 130° C. After cooling, the reaction mixture was poured into ice-water (500 ml) and the precipitate separated. This was recrystallised from diisopropyl ether/hexane to give pure benzyl 4-(2,2,2-trifluoroethoxy)phenyl ketone.

Workup

  1. additionwas added dropwise over 30 minutes
  2. temperatureAfter cooling
  3. customthe precipitate separated
  4. customThis was recrystallised from diisopropyl ether/hexane

Sources & evidence

ORD record
ord-56516d223db747e3a9fa16272e1e4e3d
Source dataset
uspto-grants-1989_12
Patent number
US04888340

Reaction notes

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