Water → HCID 18915760, compound

HRID 1292587Notes

Reaction equation

HRID 1292587 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]([OH:16])[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].Br[CH:23]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH3:24].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C(C)=CC=CC=1.CN(C)C(=O)C>[OH:1][C:2]1[CH:15]=[C:14]([O:16][CH:23]([CH3:24])[CH2:25][CH:26]([CH3:28])[CH3:27])[C:13]([C:17]([CH3:20])([CH3:21])[CH2:18][CH3:19])=[CH:12][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 121776Pentane, 2-bromo-4-methyl-HCID 18915766HCID 18915766, compound

Product 1

HCID 18915760HCID 18915760, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 10 g (35 mmol) of 2,4-dihydroxy-5-(1,1-dimethylpropyl)benzophenone, 11 g (66 mmol) of 2-bromo-4-methylpentane and 9.7 g (70 mmol) of potassium carbonate in 50 ml of xylene and 20 ml of N,N-dimethylacetamide is heated with stirring and held at 125° C. for 6 h. The reaction mixture is cooled, then treated with 30 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 (200° C./0. 1 mbar). 11.2 g (86.4%) of the compound are obtained as a yellow liquid.

Workup

  1. temperatureis heated
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted with ethyl acetate
  4. washThe resulting solution is washed with water
  5. dry with materialafter drying over MgSO4
  6. filtrationfiltering
  7. concentrationconcentrating by evaporation
  8. distillationis distilled in a bulb tube (200° C./0. 1 mbar)

Sources & evidence

ORD record
ord-dc5cfc4f2fd647f5a9843b8822a969d5
Source dataset
uspto-grants-1998_05
Patent number
US05756793

Reaction notes

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