Ethylene Glycol → HCID 21298517, compound

HRID 653042Notes

Reaction equation

HRID 653042 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)=[O:3].[CH2:11](O)[CH2:12][OH:13].B(F)(F)F>C1C=CC=CC=1>[CH3:1][C:2]1([C:4]2[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=2)[O:13][CH:12]=[CH:11][O:3]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6356Boron trifluorideHCID 7466p-Bromoacetophenone

Product 1

HCID 21298517HCID 21298517, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 4-Bromoacetophenone (50.0 g., 0.25 mol) in 500 ml. benzene was added ethylene glycol (21.7 ml., 24.2 g., 0.39 mol) followed by BF3 etherate (3.69 ml., 4.26 g., 0.03 mol). The mixture was heated at reflux with a Dean-Stark trap, cooled, washed 1×350 ml. saturated NaHCO3, dried and stripped to yield title product as an oil which crystallized on standing 60.2 g., recrystallized from pentane (chilled in an acetone-dry ice bath) 43.6 g.; 1H-nmr 1.6 (s, 3H), 3.75 (m, 2H), 4.0 (m, 2H), 7.3 (d, 2H), 7.45 (d, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux with a Dean-Stark trap
  3. temperaturecooled
  4. washwashed 1×350 ml
  5. dry with materialsaturated NaHCO3, dried

Sources & evidence

ORD record
ord-cc81015780164861aa836025007604d1
Source dataset
uspto-grants-1987_06
Patent number
US04675186

Reaction notes

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