Ethylene Glycol → HCID 23507886, compound

HRID 2258644Notes

Reaction equation

HRID 2258644 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[CH2:9]2)=[CH:4][CH:3]=1.[CH2:13](O)[CH2:14][OH:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.C(OCC)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 36915747-Bromo-2-tetralone

Product 1

HCID 23507886HCID 23507886, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 7-bromo-2-tetralone (1.1 g, 4.9 mmol), ethylene glycol (0.62 g, 10 mmol), and p-toluensulfonic acid (80 mg, 0.42 mmol) in benzene (20 ml) was stirred under N2 at reflux utilizing a Dean-Stark trap for 45 minutes. The cooled solution was diluted with diethyl ether (60 ml), washed with saturated NaHCO3 solution (2×10 ml), dried (MgSO4) and concentrated in vacuo to give 7'-bromo-3',4'-dihydrospiro[1,3-dioxolane-2,2'(1'H)-naphthalene] as an oil (1.2 g). 1H NMR (CDCl3, 200 MHz) δ: 1.95 (t, J=7 Hz, 2H, CH2), 2.91 (t, J=7 Hz, 2H, CH2), 2.95 (s, 2H, CH2), 4.01 (s, 4H, OCH2CH2O), 6.97 (d, J=8 Hz, 1H, Ar), 7.15-7.27 (m, 2H, Ar).

Workup

  1. temperatureat reflux
  2. customfor 45 minutes
  3. washwashed with saturated NaHCO3 solution (2×10 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a53c83fbf799471e882d83b6fa92da3c
Source dataset
uspto-grants-1997_08
Patent number
US05661155

Reaction notes

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