4-Hydroxybenzyl Alcohol → (4-(Prop-2-en-1-yloxy)phenyl)methanol

HRID 2381577Notes

Reaction equation

HRID 2381577 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[CH2:10](Br)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)[CH:11]=[CH2:10]

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 11744970(4-(Prop-2-en-1-yloxy)phenyl)methanolYield 71%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxybenzylalcohol (1.52 g, 12.2 mmol.), allyl bromide (1.1 ml, 12.2 mmol.), acetonitrile (40 ml), and potassium carbonate (2.54 g, 18.4 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 (0.72 g, 71%). 1H NMR (300 MHz, CDCl3) δ 2.1 (s, 1H), 4.55 (m, 2H), 4.6 (s, 2H), 5.3 (d, 1H, J=11.5 Hz), 5.43 (d, 1H, J=16.5 Hz), 6.1 (m, 1H), 6.94 (m, 2H), 7.33 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 65.3, 69.2, 115.2, 118.1, 129.0, 129.4, 133.7, 158.6.

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-f1b75fb3aee1484caf749f389fa6ef08
Source dataset
uspto-grants-2012_09
Patent number
US08258175B2

Reaction notes

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