Water → HCID 19099814, compound

HRID 2253886Notes

Reaction equation

HRID 2253886 reaction equation
C[C:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=C)CC=1.[F:11][C:12]([F:20])([F:19])[C:13]([C:15]([F:18])([F:17])[F:16])=[O:14].[OH2:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:11][C:12]([F:20])([F:19])[C:13]1([C:15]([F:18])([F:17])[F:16])[O:21][CH:5]([CH:8]=[CH2:10])[CH:6]([CH:7]=[CH2:2])[O:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 12695HexafluoroacetoneHCID 440917(+)-Limonene

Product 1

HCID 19099814HCID 19099814, compoundYield 779.5%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Conditions

Temperature
120 °C

Procedure

2,3-Divinylethylene oxide was prepared according to E. L. Stogryn et al., J. Org. Chem., 29, 1275 (1964). This compound (60 g, 0.625 mole) was mixed with d-limonene (2 g), tetra-n-butylammonium bromide (0.6 g), water (0.6 g) and hexafluoroacetone (108 g, 0.65 mole) in a 360 ml Shaker tube. The tube was sealed and was heated at 80° C./1 h4, 100° C./1hr and 120° C./6 hrs. The product mixture unloaded from the tube was distilled to give the desired product 30 g as a clear, colorless liquid. Bp. 50° C./30 mmHg. The structure was supported by its NMR spectroscopic data.

Workup

  1. customThe tube was sealed
  2. distillationwas distilled

Sources & evidence

ORD record
ord-092649497cf14ab1b786e48366efada0
Source dataset
uspto-grants-1993_08
Patent number
US05233058

Reaction notes

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