Dimethyl Sulfate → Methyl 2,6-bis(trifluoromethyl)benzoate

HRID 1720084Notes

Reaction equation

HRID 1720084 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[C:4]=1[C:5]([OH:7])=[O:6].[OH-].[Na+].S(OC)(O[CH3:24])(=O)=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:15])[F:14])[C:4]=1[C:5]([O:7][CH3:24])=[O:6]

Participants

6

Reactant 4

HCID 6497Dimethyl Sulfate2×HCID 14798Sodium HydroxideHCID 906182,6-Bis(trifluoromethyl)benzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 22420073Methyl 2,6-bis(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6 g of 2,6-bis-trifluoromethyl-benzoic acid, 60 ml of tetrahydrofuran and 11.58 ml of a 2N sodium hydroxide solution was stirred for 30 minutes at 20° C. and after the reaction medium was cooled to 0° C., 4.26 ml of dimethyl sulfate were added. The mixture was stirred for 1 hour at 20° C. and another 2.1 ml of dimethyl sulfate were added. The reaction mixture was stirred for 24 hours at 20° C. and was then poured into an aqueous solution of sodium bicarbonate, extracted with isopropyl ether, then with ethyl acetate, dried, filtered, rinsed and brought to dryness. After chromatographing on silica (eluant hexane-ethyl acetate (9-1)), 5.59 g of the desired product were obtained.

Workup

  1. stirringThe reaction mixture was stirred for 24 hours at 20° C.
  2. extractionextracted with isopropyl ether
  3. dry with materialwith ethyl acetate, dried
  4. filtrationfiltered
  5. washrinsed

Sources & evidence

ORD record
ord-10051caaf91948bb9e33dbc7b71de408
Source dataset
uspto-grants-1996_04
Patent number
US05504112

Reaction notes

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