Allyl bromide → HCID 67151185, compound

HRID 2387590Notes

Reaction equation

HRID 2387590 reaction equation
[CH3:1][C:2]([O-])(C)[CH3:3].[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[C:15](\[CH3:18])/[CH2:16][OH:17])=[CH:10][CH:9]=1.C(Br)C=C>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([O:17][CH2:16]/[C:15](/[CH3:18])=[CH:14]/[C:11]1[CH:12]=[CH:13][C:8]([CH3:7])=[CH:9][CH:10]=1)[CH:2]=[CH2:1]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 156834112-Propen-1-ol, 2-methyl-3-(4-methylphenyl)-, (2E)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 67151185HCID 67151185, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Solid potassium tert-butylate (47 g, 0.411 mol) was added portion-wise to a solution of E-3-(4-methylphenyl)-2-methyl-2-propen-1-ol (68.05 g, 0.420 mol) in dry THF (800 ml) at room temperature under nitrogen (exothermic to 30° C.). After 1 more hour at room temperature, the reaction was cooled to 5° C. and tetra butyl ammonium iodide (7.9 g, 0.021 mol) was added followed by allyl bromide (102.65 g, 0.840 mol) drop-wise. The reaction was warmed up to room temperature overnight and poured onto water (800 ml). The reaction was extracted twice with ethyl acetate. Each organic phase was washed with water and brine. Combined extracts were 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 under vacuum through a 20-cm Widmer column. 79 g of the desired product were obtained (yield=93%). B.P.=82° C./0.001 mbar

Workup

  1. temperatureThe reaction was warmed up to room temperature overnight
  2. additionpoured onto water (800 ml)
  3. extractionThe reaction was extracted twice with ethyl acetate
  4. washEach organic phase was washed with water and brine
  5. dry with materialCombined extracts were 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 under vacuum through a 20-cm Widmer column

Sources & evidence

ORD record
ord-b11cc0977e914d3d80169bad418f489d
Source dataset
uspto-grants-2012_09
Patent number
US08268895B2

Reaction notes

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