Allyl bromide → HCID 28562283, compound

HRID 2381578Notes

Reaction equation

HRID 2381578 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6].[CH2:12](Br)[CH:13]=[CH2:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:14]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6])[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 780893-Hydroxy-4-methoxybenzyl alcohol

Product 1

HCID 28562283HCID 28562283, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-hydroxy-4-methoxybenzylalcohol (0.80 g, 7.79 mmol.), allyl bromide (0.45 ml, 5.9 mmol.), acetonitrile (20 ml), and potassium carbonate (1.08 g, 7.8 mmol.) was reluxed for 18 hours, then concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water and brine. The organic layer was dried (MgSO4) and evaporated to give the product as a yellow oil (1.14 g, 57%). 1H NMR (300 MHz, CDCl3) δ 1.90 (s, 1H), 3.79 (s, 3H), 4.52-4.54 (m, 4H), 5.2 (d, 1H, J=12 Hz), 5.32 (d, 1H, J=17.25 Hz), 6.0 (m, 1H), 6.77 (s, 2H), 6.85 (s, 1H); 13C NMR (75 MHz, CDCl3) δ 56.3, 65.6, 70.3, 111.2, 113.6, 118.4, 119.7, 133.7, 134.4, 147.8, 149.9.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-12c51837408845f39c5ef8eaa7a6e5dc
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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