Iodoethane → 2'-Ethoxyl-1,1'-biphenyl-2-ol

HRID 844591

Reaction equation

HRID 844591 reaction equation
[C:1]1([OH:14])[C:2]([C:7]2[C:8]([OH:13])=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:3][CH:4]=[CH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][CH3:23]>CC(C)=O>[O:14]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8]([OH:13])=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

HCID 226138842'-Ethoxyl-1,1'-biphenyl-2-ol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2′-Ethoxyl-1,1′-biphenyl-2-ol was prepared by modifying the procedure reported in J. Org. Chem. 1981, 46, 4988. In 50 mL of acetone was added 10 g of 2,2′-biphenol and 9.4 g of potassium carbonate. After stirring at room temperature for one hour, a solution of iodoethane (9.2 g in 10 mL of acetone) was added slowly dropwise. The mixture was filtered, washed with acetone, and solvent removed by rotary evaporation. The residue was flashed chromatographed to give 5.1 g of the2′-ethoxyl-1,1′-biphenyl-2-ol as a colorless oil. 1H NMR (C6D6): 7.20 (m, 3H), 7.10 (m, 1H), 7.05 (m, 1H), 6.85 (m, 2H), 6.55 (m, 1H), 3.38 (q, 2H), 0.81 (t, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with acetone, and solvent
  3. customremoved by rotary evaporation
  4. customThe residue was flashed chromatographed

Sources & evidence

ORD record
ord-6e2e9ef1e87a416cb7b3c19e96d2e5b2
Source dataset
uspto-grants-2002_04
Patent number
US06380421B1

Linked notes

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