Allyl chloride → (1E)-[3-(allyloxy)-2-methyl-1-propenyl]benzene

HRID 2387596Notes

Reaction equation

HRID 2387596 reaction equation
[CH3:1][C:2]([O-])(C)[CH3:3].[K+].[CH3:7]/[C:8](/[CH2:16][OH:17])=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(Cl)C=C>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([O:17][CH2:16]/[C:8](/[CH3:7])=[CH:9]/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:2]=[CH2:1]

Participants

6

Reactant 3

HCID 7850Allyl chlorideHCID 6393846alpha-Methylcinnamic alcoholHCID 23665647Potassium tert-butoxide

Product 1

HCID 67330776(1E)-[3-(allyloxy)-2-methyl-1-propenyl]benzeneYield 67.4%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Solid potassium tert-butylate (110 g, 0.960 mol) was added portion-wise (1 hour) to a solution of trans-2-methyl-3-phenyl-2-propen-1-ol (100 g, 0.950 mol) in dry THF (1 liter) at room temperature under nitrogen. After 1 more hour at room temperature, the reaction was cooled to 5° C. and tetra butyl ammonium iodide (12.1 g, 0.032 mol) was added followed by allyl chloride (100 g, 1.280 mol) drop-wise. The reaction was warmed up to room temperature overnight and poured onto water (2 liters). The reaction was extracted twice with ethyl acetate. Each organic phase was washed with water and brine. Combined extracts are dried over solid anhydrous sodium sulfate. The solid was filtered off, rinsed with diethyl ether and the solvents were removed under vacuum. The product was purified by distillation through a 20-cm Widmer column. 120.5 g of the desired compound was obtained (97% pure, 0.620 mol, 97%). B.P.=70° C./0.067 mbar

Workup

  1. temperatureThe reaction was warmed up to room temperature overnight
  2. additionpoured onto water (2 liters)
  3. extractionThe reaction was extracted twice with ethyl acetate
  4. washEach organic phase was washed with water and brine
  5. dry with materialCombined extracts are dried over solid anhydrous sodium sulfate
  6. filtrationThe solid was filtered off
  7. washrinsed with diethyl ether
  8. customthe solvents were removed under vacuum
  9. distillationThe product was purified by distillation through a 20-cm Widmer column

Sources & evidence

ORD record
ord-925a07e31ca04ad1880aac45469ad791
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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