1,2-Dibromoethane → HCID 19747006, compound

HRID 372935Notes

Reaction equation

HRID 372935 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[OH-].[Na+].[Br:19][CH2:20][CH2:21]Br>O.C(O)C.CC(C)=O>[Br:19][CH2:20][CH2:21][O:16][C:14]1[CH:13]=[CH:12][C:3]([C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:5])=[C:2]([OH:1])[CH:15]=1

Participants

7

Reactant 3

HCID 78391,2-DibromoethaneHCID 85722,4-DihydroxybenzophenoneHCID 14798Sodium Hydroxide

Product 1

HCID 19747006HCID 19747006, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 2000 mL, 1 neck round-bottomed flask containing a magnetic stir bar is charged with 2,4-dihydroxybenzophenone (85.6 g, 0.40 mol, Aldrich Chemical Co., Milwaukee, Wis.). To this is added a solution of sodium hydroxide (16.0 g) dissolved in 320 mL of water. Next, 1,2-dibromoethane (105.6 g, 0.56 mol) dissolved in 320 ml of ethanol is added. The reaction mixture is heated to reflux with stirring for 16 hours. The reaction vessel is then transferred to a rotary evaporator where the liquids are removed at aspirator pressure at 80° C. A brown solid is obtained which is suspended in 180 mL of acetone and stirred for 1 hour at 45° C. This mixture is filtered and the filtrate poured into 2 L of water containing 20 g of sodium carbonate yielding 65 grams of a tan precipitate. This material is recrystallized from approximately 100 mL of ethanol to give 55.3 g (0.17 mol, 43%) of a light tan solid m.p. 87°-89.5° C.

Workup

  1. additionA 2000 mL, 1 neck round-bottomed flask containing a magnetic stir bar
  2. additionis added
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux
  5. customThe reaction vessel is then transferred to a rotary evaporator where the liquids
  6. customare removed at aspirator pressure at 80° C
  7. customA brown solid is obtained which
  8. stirringstirred for 1 hour at 45° C
  9. filtrationThis mixture is filtered
  10. additionthe filtrate poured into 2 L of water containing 20 g of sodium carbonate yielding 65 grams of a tan precipitate
  11. customThis material is recrystallized from approximately 100 mL of ethanol

Sources & evidence

ORD record
ord-aa6f86e81f844ca99613059b3ce9d233
Source dataset
uspto-grants-1992_11
Patent number
US05160731

Reaction notes

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