3-Phenylprop-2-En-1-Ol → HCID 12561033, compound

HRID 2387598Notes

Reaction equation

HRID 2387598 reaction equation
[H-].[Na+].[CH2:3]([OH:12])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:13](Cl)[CH:14]=[CH2:15]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:15]([O:12][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 3083-Phenylprop-2-En-1-OlHCID 7850Allyl chlorideHCID 24758Sodium hydride

Product 1

HCID 12561033HCID 12561033, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 26 g, 0.60 mol) was added portion-wise to a solution of cinnamyl alcohol (40 g, 0.29 mol) in dry THF (600 ml) at 5° C. under nitrogen. The reaction was warmed up to room temperature then refluxed. After 30 minutes, tetra butyl ammonium iodide (4 g, 0.011 mol) was added followed by allyl chloride (45.6 g, 0.60 mol) over a 1 h-period. The reaction was allowed reaching room temperature overnight, before being poured onto water. The organic phase was washed with water (3 times) and brine. Each aqueous phase was re-extracted with heptanes. Combined extracts were dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with heptanes and the solvents were removed under vacuum. The product was purified by bulb-to-bulb distillation (80° C./0.062 mbar). 50 g of the desired compound were obtained (0.287 mol, 99%).

Workup

  1. temperaturethen refluxed
  2. waitThe reaction was allowed reaching room temperature overnight
  3. additionbefore being poured onto water
  4. washThe organic phase was washed with water (3 times) and brine
  5. extractionEach aqueous phase was re-extracted with heptanes
  6. dry with materialCombined extracts were dried over solid anhydrous sodium sulfate
  7. filtrationThe solid was filtered off
  8. washrinsed with heptanes
  9. customthe solvents were removed under vacuum
  10. distillationThe product was purified by bulb-to-bulb distillation (80° C./0.062 mbar)

Sources & evidence

ORD record
ord-cd1ae5b1aea842d2b9a1a2b65c5519fb
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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