Resorcinol → 3-(Allyloxy)phenol

HRID 246902Notes

Reaction equation

HRID 246902 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[CH2:9](Br)[CH:10]=[CH2:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)[CH:10]=[CH2:9]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 7841Allyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 53141523-(Allyloxy)phenol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of resorcinol (40 g, 0.4 mol) and allyl bromide (32 g, 0.26 mol) in acetone (500 ml) containing potassium carbonate (55 g, 0.4 mol) was heated, with stirring, under reflux for 10 hours. The mixture was filtered, and the filtrate was evaporated to dryness. The residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min using hexane-ethyl acetate (8:1, v/v) as a liquid phase. 3-Allyloxyphenol was isolated as a colorless oil (20 g, 51% based on ally bromide); NMR (chloroform-d): δ4.78 (s, OH), 4.55 (d, J=5.5 Hz, CH2CH=CH2), 5.29-5.50 (m, CH2CH=CH2), 6.07 (m, CH2CH=CH2), 7.18 (t, J=8.5 Hz, H-5), 6.46-6.58 (m, remaining Ar--H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by means of PrepPak 500/silica on a Waters Associates Prep LC/System 500 at 250 ml/min

Sources & evidence

ORD record
ord-36d047b974804750968f713207bb05ee
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Reaction notes

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