Water → HCID 18915769, compound

HRID 725716Notes

Reaction equation

HRID 725716 reaction equation
O[C:2]1[CH:15]=[C:14](O)[C:13]([C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[OH2:30]>C1(C)C(C)=CC=CC=1>[OH:30][C:2]1[CH:15]=[C:14]([CH2:17][CH2:13][CH2:14][CH2:15][CH2:2][CH:3]([CH3:12])[CH3:4])[C:13]([C:17]([CH3:21])([CH3:20])[CH2:18][CH3:19])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 18915766HCID 18915766, compound

Product 1

HCID 18915769HCID 18915769, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10 g (35 mmol) of 2,4-dihydroxy-5-(1,1-dimethylpropyl)benzophenone, 7.9 g (38 mmol) of iso-bromooctane (mixture of isomers), 9.7 g (70 mmol) of potassium carbonate and 0.6 g (3.5 mmol) of potassium iodide in 30 ml of xylene is stirred at 110° C. for 8 h. The reaction mixture is cooled, then treated with 100 ml of water and extracted with ethyl acetate. The resulting solution is washed with water and then with saturated sodium chloride solution. The residue which remains after drying over MgSO4, filtering and concentrating by evaporation is distilled in a bulb tube (190° C./4 mbar). 11.2 g (86.4%) of the compound are obtained as a yellow liquid.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe resulting solution is washed with water
  4. dry with materialafter drying over MgSO4
  5. filtrationfiltering
  6. concentrationconcentrating by evaporation
  7. distillationis distilled in a bulb tube (190° C./4 mbar)

Sources & evidence

ORD record
ord-7947166ea74b49b19a9487db2ffa5ed0
Source dataset
uspto-grants-1998_01
Patent number
US05707690

Reaction notes

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