Phenethyl bromide → HCID 86733796, compound

HRID 1282912Notes

Reaction equation

HRID 1282912 reaction equation
[CH3:1][CH:2]([C:7]1[CH:8]=[C:9]([OH:25])[C:10]2[CH:11]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:12][C:13]([CH3:18])([CH3:17])[O:14][C:15]=2[CH:16]=1)[CH2:3][CH2:4][CH2:5][CH3:6].[C:26]1([CH2:32][CH2:33][Br:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CC(C)=O>[Br-:34].[C:26]1([CH2:32][CH2:33][N+:22]2[CH:21]=[CH:20][C:19]([CH:11]3[C:10]4[C:15](=[CH:16][C:7]([CH:2]([CH2:3][CH2:4][CH2:5][CH3:6])[CH3:1])=[CH:8][C:9]=4[OH:25])[O:14][C:13]([CH3:18])([CH3:17])[CH2:12]3)=[CH:24][CH:23]=2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7666Phenethyl bromideHCID 54415854HCID 54415854, compound

Product 1

HCID 86733796HCID 86733796, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-(2-Hexyl)-2,2-dimethyl-4-(4-pyridyl) chroman-5-ol (5.45 g, 0.016 mole) and 2-phenylethyl bromide (3.70 g, 0.020 mole) were dissolved in acetone (120 ml) and the solution was refluxed for 4 days. The solution was then allowed to cool and the resulting precipitate was filtered, washed with acetone and dried to yield 1-(2-phenylethyl)-4-[7-(2-hexyl)-2,2-dimethyl-5-hydroxychroman-4-yl] pyridinium bromide (7.22 g, 88%) as colourless microcrystals, m.p. 232°-235°C.

Workup

  1. temperaturethe solution was refluxed for 4 days
  2. temperatureto cool
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with acetone
  5. customdried

Sources & evidence

ORD record
ord-4fa7252c73e04a67b6311b5d41133bc1
Source dataset
uspto-grants-1976_08
Patent number
US03973023

Reaction notes

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