Sodium Hydroxide → HCID 10783651, compound

HRID 612589Notes

Reaction equation

HRID 612589 reaction equation
[I-].[CH:2]([O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:21])[CH3:20])=[CH:14][C:13]=2[O:22][CH3:23])=[C:10]([C:24]2[O:25]CC(C)(C)[N+]=2C)[CH:9]=[CH:8][CH:7]=1)([CH3:4])[CH3:3].[OH-:32].[Na+]>CO>[CH:2]([O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([C:24]([OH:25])=[O:32])[C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]([CH3:20])[CH3:21])=[CH:14][C:13]=1[O:22][CH3:23])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10697687HCID 10697687, compound

Product 1

HCID 10783651HCID 10783651, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepare a solution of 2-(6,4'-diisopropyloxy-2 '-methoxy-biphenyl-2-yl)-3,4,4-trimethyl-oxazolinium iodide (13.20 g, 0.0245 mole) in 20% NaOH (140 mL) and methanol (140 mL) and stir at reflux overnight. Concentrate the resulting colorless solution on the rotovap until precipitation begins. Dilute the resulting suspension to 300 mL with water and acidify with concentrated HCl to pH=1. Extract the precipitate into CH2Cl2 (400 mL), wash with brine, separate and dry over MgSO4. Filter, concentrate and recrystallize from cyclohexane (~175 mL) to obtain the title compound (7.10 g, 84%). m.p. 117-119° C.

Workup

  1. temperatureat reflux overnight
  2. concentrationConcentrate the resulting colorless solution on the rotovap
  3. customuntil precipitation
  4. additionDilute the resulting suspension to 300 mL with water
  5. extractionExtract the precipitate into CH2Cl2 (400 mL)
  6. washwash with brine
  7. customseparate
  8. dry with materialdry over MgSO4
  9. filtrationFilter
  10. concentrationconcentrate
  11. customrecrystallize from cyclohexane (~175 mL)

Sources & evidence

ORD record
ord-2992bf2d570a42a48a2c5e265a51ebb1
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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