Ethylene Glycol → HCID 22910085, compound

HRID 1078124Notes

Reaction equation

HRID 1078124 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=[O:18])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19](O)[CH2:20][OH:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:12]1([CH2:11][CH2:10][C:9]2([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:21][CH2:20][CH2:19][O:18]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 214961,5-Diphenylpentan-3-oneHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 22910085HCID 22910085, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 135 mg (0.6 mmol) of 1,5-diphenyl-3-pentanone, 0.2 ml of ethylene glycol, and 10 mg of p-toluene sulfonic acid monohydrate was refluxed with azeotropic removal of water. After separation of water was completed, the solution was diluted with ethyl acetate, washed sequentially with aqueous NaHCO and water, dried over Na2SO4, and concentrated to provide the desired compound. 1H NMR (CDCl3) δ2.0 (m, 4H), 2.71 (m, 4H), 4.03 (s, 4H), 7.15-7.3 (m, 10H). Mass spectrum: (M+H)+ =283.

Workup

  1. customAfter separation of water
  2. additionthe solution was diluted with ethyl acetate
  3. washwashed sequentially with aqueous NaHCO and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ad76cbabd11e4280ba1046d18c1ad16c
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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