Hydrochloric Acid → 3-(4-tert-Butylphenyl)-1-propene

HRID 375585Notes

Reaction equation

HRID 375585 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1.Cl[CH2:14][CH:15]=[CH2:16].Cl>CCOCC>[CH3:10][C:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:16][CH:15]=[CH2:14])=[CH:4][CH:5]=1)([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7850Allyl chlorideHCID 775951-Bromo-4-tert-butylbenzeneHCID 5462224Magnesium

Product 1

HCID 27573173-(4-tert-Butylphenyl)-1-propeneYield 48.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a Grignard reagent prepared from 12 g magnesium, 250 ml ether and 100 g 1-bromo-4-(1,1-dimethylethyl)benzene were added 50 g 3-chloro-1-propene dissolved in 150 ml ether. After the addition, the mixture was refluxed for one hour and kept stirring overnight at room temperature. The reaction mixture was then poured onto crushed ice and acidified with hydrochloric acid to dissolve any precipitated solid. The ether solution was separated, washed with water, and dried with anhydrous sodium sulfate, solvent removed and product distilled to provide 40 g of 1-(1,1-dimethylethyl)-4-(2-propenyl)benzene, listed in Table 1 as compound I-1. The product was characterized by a boiling point of 65°-66° C. at a pressure of 0.25 mm Hg.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for one hour
  3. additionThe reaction mixture was then poured
  4. customonto crushed ice
  5. dissolutionto dissolve any precipitated solid
  6. customThe ether solution was separated
  7. washwashed with water
  8. dry with materialdried with anhydrous sodium sulfate, solvent
  9. customremoved
  10. distillationproduct distilled

Sources & evidence

ORD record
ord-f337e9ce84364569b3af72ca36fde65b
Source dataset
uspto-grants-1996_01
Patent number
US05486533

Reaction notes

Loading…