Water → 3-Methoxy-1,1,1,5,5,5-hexafluoropent-2-ene

HRID 1421116Notes

Reaction equation

HRID 1421116 reaction equation
[F:1][C:2]([CH:5]=[C:6]=[CH:7][C:8]([F:11])([F:10])[F:9])([F:4])[F:3].[O:12]([CH3:14])[Na].O>CO>[C:2]([CH:5]=[C:6]([CH2:7][C:8]([F:9])([F:10])[F:11])[O:12][CH3:14])([F:4])([F:3])[F:1]

Participants

5

Reactant 3

HCID 962WaterHCID 10844993HCID 10844993, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 541695823-Methoxy-1,1,1,5,5,5-hexafluoropent-2-eneYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21.1 g (0.12 mol) of bis(trifluoromethyl)allene were added to 20 mL 0.5 N NaOCH3 in methanol (8 mol % relative to allene) over 1 h with water bath cooling, keeping the reaction temperature at 10-20° C. Stirring was continued for 15 min. and the mixture poured into 80 mL cold water. The lower layer was separated and the aqueous portion extracted with 20 mL CH2Cl2. The combined organic layers were washed with 5 mL brine, dried (Na2SO4) and distilled to give 21.9 g (88% yield) of CF3CH=C(OCH3)CH2CF3, boiling point 110-111° C. IR: 1672 cm-1. Major MS fragments: 208 (75.9), 189 (30.2), 158 (31.6), 125 (60.5), 111 (82.4), 91 (100), 31 (91.2). 1H NMR:4.95 (q,1H, J=7.5 Hz), 3.65 (s, 3H), 3.18 (q, 2H, J=9.8 Hz) ppm. 19FNMR: -54.4(d,3 F), -63.9 (t, 3 F) ppm. Anal. Calcd for C6H6F6O: C, 34.61; H, 2.91. Found: C, 34.59; H. 2.85.

Workup

  1. temperaturecooling
  2. customat 10-20° C
  3. customThe lower layer was separated
  4. extractionthe aqueous portion extracted with 20 mL CH2Cl2
  5. washThe combined organic layers were washed with 5 mL brine
  6. dry with materialdried (Na2SO4)
  7. distillationdistilled

Sources & evidence

ORD record
ord-14f059a6d04944b095c86e650401e0f0
Source dataset
uspto-grants-2000_06
Patent number
US06072088

Reaction notes

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