Dimethyl Sulfate → HCID 20030479, compound

HRID 1632152Notes

Reaction equation

HRID 1632152 reaction equation
[C:1]([S:5][C:6]([F:14])([F:13])[C:7]([F:12])([F:11])[C:8]([O-:10])=[O:9])([CH3:4])([CH3:3])[CH3:2].[Na+].S(OC)(O[CH3:20])(=O)=O>>[C:1]([S:5][C:6]([F:14])([F:13])[C:7]([F:11])([F:12])[C:8]([O:10][CH3:20])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 23683596HCID 23683596, compound

Product 1

HCID 20030479HCID 20030479, compoundYield 42%

Procedure

The resulting dark solution, which contained sodium 3-t-butylthiotetrafluoropropionate, was stirred with 69.3 g (0.55 mole) of dimethyl sulfate while the temperature was maintained at 30°. After an initial exothermic reaction subsided, the mixture was stirred overnight and then distilled to give a crude product with bp about 45° (2 mm, 2.6×10-1 kPa). The distillate was washed with 1 liter of water, dried and fractionated to give 52.1 g (42%) of methyl 3-t-butylthiotetrafluoropropionate, bp 55° (2 mm, 2.6×10-1 kPa). IR (neat): 2970 (sat'd CH), 1775 (C=O), 1100-1250 cm-1 (CF). NMR (CCl4): 1H 3.87 (s, 3H, OCH3) and 1.52 ppm (s, 9H, C(CH3)3 ; 19F -86.3 (t, JFF 7.1 Hz, 2F, CF2S) and -117.6 ppm (t, JFF 7.1 Hz, 2F, CF2C=O).

Workup

  1. temperaturewas maintained at 30°
  2. customAfter an initial exothermic reaction
  3. distillationdistilled
  4. customto give a crude product with bp about 45° (2 mm, 2.6×10-1 kPa)
  5. washThe distillate was washed with 1 liter of water
  6. customdried

Sources & evidence

ORD record
ord-44214bd59a87453d82b408614438992e
Source dataset
uspto-grants-1984_10
Patent number
US04474700

Reaction notes

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