Phenol → HCID 13839475, compound

HRID 847588Notes

Reaction equation

HRID 847588 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:8].[Na+].Cl[CH2:11][C:12]([CH2:14]Cl)=[CH2:13]>O1CCOCC1>[O:7]([CH2:11][C:12]([CH2:14][O:8][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH2:13])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 158593-Chloro-2-chloromethyl-1-propene

Product 1

HCID 13839475HCID 13839475, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2.0 ml (22.7 mmol) of phenol in 40 ml of dioxane was heated to reflux and treated with 0.96 g (23.8 mmol) of sodium hydroxide. After the solid had dissolved, the solution was treated dropwise over a period of 15 min with 1.25 ml (10.8 mmol) of 2-chloromethyl-3-chloro-1-propene. The resulting solution was heated at reflux for 6 h, allowed to cool, and concentrated in vacuo. The residue was taken up in ether, washed with several portions of water, dried over MgSO4, and concentrated to a yellow liquid. Flash chromatography using 10% ethyl acetate in hexane gave 1.72 g (65%) of the desired compound as a colorless oil. 1H NMR (CDCl3) δ 4.63 (m, 4H), 5.35-5.45 (m, 2H), 6.9-7.0 (m, 6H), 7.25-7.35 (m, 4H). Mass spectrum (M +NH4)+ =258.

Workup

  1. temperatureto reflux
  2. dissolutionAfter the solid had dissolved
  3. temperatureThe resulting solution was heated
  4. temperatureat reflux for 6 h
  5. temperatureto cool
  6. concentrationconcentrated in vacuo
  7. washwashed with several portions of water
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to a yellow liquid

Sources & evidence

ORD record
ord-9bc2a41ae2094985bbce48ef122b2b68
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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