Water → HCID 18000287, compound

HRID 2101413Notes

Reaction equation

HRID 2101413 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([C:7]([OH:10])([CH3:9])[CH3:8])=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O.CCOC(C)=O.O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:11][C:1]1[CH:2]=[CH:3][C:4]([C:7]([OH:10])([CH3:8])[CH3:9])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14529p-Cymen-8-olHCID 67184N-bromobutanimide

Product 1

HCID 18000287HCID 18000287, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of 2-p-tolylpropan-2-ol (500 mg, 3.3 mmol) in carbon tetrachloride at room temperature under argon was added N-bromosuccinimide (590 mg, 3.3 mmol), followed by benzoyl peroxide (16 mg, 0.06 mmol). The reaction mixture was stirred at reflux for 4 h. The reaction mixture was concentrated under reduced pressure to obtain a colorless gum. EtOAc (20 mL) and water (20 mL) were added and the layers were separated. The organic layer was dried (MgSO4), filtered and concentrated under vacuum to obtain crude product, which was purified by flash chromatography (silica gel column eluted with 30% EtOAc/hexanes) to isolate 620 mg of the title compound as a colorless gum. HPLC/MS: retention time=2.908 min, [M+H—H2O]+=211.

Workup

  1. temperatureat reflux for 4 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto obtain a colorless gum
  4. customthe layers were separated
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto obtain crude product, which
  9. customwas purified by flash chromatography (silica gel column eluted with 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e03cbbf2f64647dd9f15b513c41caf69
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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