1,5-Hexadiene → 131719-68-1

HRID 494543Notes

Reaction equation

HRID 494543 reaction equation
[CH:1]1([CH:7](O)[CH:8]=[CH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C=CCCC=C.S(Br)([Br:19])=O>ClCCCl>[Br:19][CH2:9]/[CH:8]=[CH:7]/[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 115981,5-HexadieneHCID 68176Thionyl bromideHCID 1381961-Cyclohexylprop-2-en-1-ol

Product 1

HCID 15752625131719-68-1Yield 43%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Example 36A (5.62 g, 40.1 mmol) and 1,5-hexadiene (3.56 mL, 30.1 mmol) in 1,2-dichloroethane (70 mL), stirring at 0° C., was added thionyl bromide (4.66 mL, 60.12 mmol). The reaction was stirred for 2 hours at 0° C. and then quenched with water. The mixture was extracted with diethyl ether and the diethyl ether layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the title compound (3.46 g, 43%). 1H NMR (300 MHz, CDCl3): δ ppm 1.16 (m, 6 H) 1.69 (m, 4 H) 1.98 (m, 1 H) 3.94 (m, 2 H) 5.65 (m, 2 H).

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe diethyl ether layer was washed with saturated sodium bicarbonate solution
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaaa16c553d443ad8a8843ea5e753430
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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