Hexane → HCID 53716405, compound

HRID 257548Notes

Reaction equation

HRID 257548 reaction equation
[CH2:1]([Li])CCC.CCCCCC.C=[PH3].[CH:14]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)=[CH:15][CH2:16][CH2:17][CH2:18][CH3:19]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH:14]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[CH2:1])=[CH:23][CH:22]=1)=[CH:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 8058HexaneHCID 54357442HCID 54357442, compoundHCID 178418339ButyllithiumHCID 178503018HCID 178503018, compound

Product 1

HCID 53716405HCID 53716405, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a 200 ml three-necked flask in a nitrogen atmosphere, anhydrous diethyl ether (150 ml), methyltriphenylphosphonium bromide (7.5 g, 21 mmol) and a 1.6N solution of n-butyllithium in hexane (13.1 ml, 21 mmol of n-butyllithium) were charged and stirred at room temperature for 5 hours to prepare methylenephosphorane. To the reaction mixture, a solution of 4-(1-hexenyloxy)benzaldehyde (4.08 g, 20 mmol) in anhydrous diethyl ether (20 ml) was dropwise added over 3 minutes. After heating the reaction mixture under reflux for one hour and removing solids by filtration, hexane (150 ml) was added to a filtrate, and an organic phase was washed with water (150 ml×3), followed by evaporating volatile components off to obtain 4-(1-hexenyloxy)styrene (3.0 g) of the formula: ##STR5##

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperatureunder reflux for one hour
  3. customremoving solids
  4. filtrationby filtration, hexane (150 ml)
  5. additionwas added to a filtrate
  6. washan organic phase was washed with water (150 ml×3)
  7. customby evaporating volatile components off

Sources & evidence

ORD record
ord-ddbe66ec0e03432a96d4095435c25e97
Source dataset
uspto-grants-1993_11
Patent number
US05262502

Reaction notes

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