Allyl bromide → α-Methyl-α-2-propen-1-ylbenzeneethanol

HRID 1388869Notes

Reaction equation

HRID 1388869 reaction equation
[CH2:1]([CH:8]([OH:10])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11](Cl)[CH:12]=C.[CH2:15](Br)C=C.C(=O)(O)[O-].[Na+]>C(O)(C)C>[CH2:9]([C:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:10])[CH3:15])[CH:11]=[CH2:12]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 7850Allyl chlorideHCID 941851-Phenyl-2-propanolHCID 516892Sodium Bicarbonate

Product 1

HCID 14223528α-Methyl-α-2-propen-1-ylbenzeneethanol

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A 2-liter autoclave was charged with benzyl ethanol hydrogenated-tallow amine (632.2 gm.; 1.5 mol), 133.9 gm. allyl chloride, 18.1 gm. allyl bromide, 160 gm. sodium bicarbonate, and 175 ml isopropyl alcohol. The mixture was allowed to react at 100° C. overnight. An aliquot was removed and found to contain 61.2% amine. The apparent slow reaction rate was due to a leak in the autoclave. When the problem was corrected, an additional 133.9 gm. of allyl chloride and 18.1 gm. allyl bromide was added. The reaction as allowed to go overnight. An aliquot was removed and analyzed. It contained 16.1% amine and 0.4% amine HCl. An additional 36 gm. of allyl bromide was added. The following day, a sample was removed, analyzed, and found to contain 7% amine and 0.5% amine HCl. Allyl bromide (15 gm.) and 25 gm. of sodium bicarbonate were added and the reaction was continued overnight. Analyses of an aliquot showed there to be 0.0% amine HCl and 5.2% amine. The autoclave was charged with methyl chloride to finish the quaternization reaction. Final analysis showed an Effective gram molecular weight of 780.7.

Workup

  1. customto react at 100° C. overnight
  2. customAn aliquot was removed
  3. additionallyl bromide was added
  4. customThe reaction
  5. customAn aliquot was removed
  6. additionof allyl bromide was added
  7. customThe following day, a sample was removed
  8. additionof sodium bicarbonate were added
  9. waitthe reaction was continued overnight
  10. additionThe autoclave was charged with methyl chloride
  11. customthe quaternization reaction

Sources & evidence

ORD record
ord-431693bede444ae2b8dbebc791a482b5
Source dataset
uspto-grants-1984_02
Patent number
US04434076

Reaction notes

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