Phenol → HCID 10800118, compound

HRID 1082140Notes

Reaction equation

HRID 1082140 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Cl.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 75102Octane, 1,8-dichloro-

Product 1

HCID 10800118HCID 10800118, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

A two phase mixture of phenol (5 g, 53 mmol), 1,8-dichlorooctane (25 ml), tetrabutylammonium hydrogensulphate (0.3 g, 1 mmol), and sodium hydroxide solution (25 ml, 6M) was refluxed for 16 h. The organic layer was separated, washed with water (2×50 ml), dried (MgSO4), and concentrated in vacuo. The residues were columned (silica; eluant: dichloromethane/petrol 1:10) to give the title compound as a colourless mobile oil (9.20 g, 72%). bp 50° C. at 4.6 mm Hg. NMR (CDCl3) δ=1.27-1.52 (8H, m), 1.70-1.81 (4H, m), 3.53 (2H,t,J=6 Hz), 3.93 (2H,t,J=6 Hz), 6.83-6.93 (3H,m), 7.00-7.10 (2H,m). IR (liq, cm-1) 2992, 2937, 2858, 1601, 1587 MS(EI) m/e=240 (M+, 1%)

Workup

  1. temperaturewas refluxed for 16 h
  2. customThe organic layer was separated
  3. washwashed with water (2×50 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-807eb5593380432d9fc257e2020f9240
Source dataset
uspto-grants-1996_12
Patent number
US05589500

Reaction notes

Loading…