Sulfuric Acid → HCID 13860680, compound

HRID 1199856Notes

Reaction equation

HRID 1199856 reaction equation
S(=O)(=O)(O)[OH:2].[CH3:6][O:7][C:8](F)(F)[C:9]([F:18])=[CH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CCCCC>[F:18]/[C:9](=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])/[C:8]([O:7][CH3:6])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54373384HCID 54373384, compound

Product 1

HCID 13860680HCID 13860680, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 3 g 75% sulfuric acid and 15 mL of n-pentane at 20° C. in a round-bottom 50 mL flask was added the crude 1-methoxy-1,1,2-trifluoro-2-decene (1.2 g). The resulting mixture was stirred for 40 hours at 20° C. The reaction mixture was poured into a large excess of ice-water and the liquid extracted twice with diethyl ether. The ether layers were combined, washed with water and brine, then dried over anhydrous magnesium sulfate. Evaporation of solvent gave a yellow oil which was chromatographed on silica gel (5% ethyl acetate in hexanes) to give 0.59 g (64.5%) of methyl (Z)-2-fluoro-2-decenoate as a clear liquid: 1H-NMR (300 MHz, CDCl3): δ 0.86(3H, t), 1.24(1OH), 2.22(2H, dq,J=2,8 Hz), 3.80(3H, s), 6.10(1H, dt, J=8, 33Hz). Mass spectrum: m/e=202 (M+ ). 19F-NMR (CDCl3): φ 131.8(d, J=33.0).

Workup

  1. extractionthe liquid extracted twice with diethyl ether
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of solvent
  5. customgave a yellow oil which
  6. customwas chromatographed on silica gel (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3f9dea65e1aa4da08aa0c774089c5db8
Source dataset
uspto-grants-1990_02
Patent number
US04902835

Reaction notes

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