Water → HCID 18406237, compound

HRID 1016222Notes

Reaction equation

HRID 1016222 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[CH2:25]([Mg]Cl)[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.O>C1COCC1>[C:14]([C:11]1[CH:10]=[C:7]([CH:8]([OH:9])[CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:12]=1[OH:13])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 178418865HCID 178418865, compound

Product 1

HCID 18406237HCID 18406237, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a 5-liter, 4-neck round-bottom flask fitted with a mechanical stirrer, reflux condenser, thermometer, and addition funnel were charged 238.5 grams (1.02 moles) of 3,5-di-t-butyl-4-hydroxybenzaldehyde and 979 grams of toluene. To this suspension, a one molar solution of phenethylmagnesium chloride in THF was slowly added such that the pot temperature slowly rose to 40° C. After the addition of several hundred milliliters of Grignard reagent solution a green sticky solid formed. The addition was halted, an additional 859 mL of toluene was added, and the solution was warmed to 80° C. The remaining Grignard reagent was slowly added while maintaining the pot temperature between 50° C. and 70° C. After the addition was complete, the reaction mixture was stirred at 70° C. for one hour. During this time, the green solids dissolved and the reaction mixture formed two liquid phases. After this time, the reaction was cooled and then quenched by slowly adding 80 mL of deionized water. The quenched reaction mixture was then poured into six liters of water. The organic phase was separated and the solvent removed in vacuo. The resulting crude product was then dissolved in warm hexane and filtered. The filtrate was washed with hexane (2×100 mL). The hexane portions were combined and solvent removed producing 242 grams (69.8 percent) of a viscous amber oil.

Workup

  1. customTo a 5-liter, 4-neck round-bottom flask fitted with a mechanical stirrer
  2. temperaturereflux condenser
  3. additionthermometer, and addition funnel
  4. customslowly rose to 40° C
  5. customformed
  6. additionThe addition
  7. temperaturewhile maintaining the pot temperature between 50° C. and 70° C
  8. additionAfter the addition
  9. dissolutionDuring this time, the green solids dissolved
  10. customthe reaction mixture formed two liquid phases
  11. temperatureAfter this time, the reaction was cooled
  12. customquenched
  13. additionby slowly adding 80 mL of deionized water
  14. customThe quenched reaction mixture
  15. customThe organic phase was separated
  16. customthe solvent removed in vacuo
  17. dissolutionThe resulting crude product was then dissolved in warm hexane
  18. filtrationfiltered
  19. washThe filtrate was washed with hexane (2×100 mL)
  20. customsolvent removed

Sources & evidence

ORD record
ord-93eb48de03fc4721a67623ae6a6d71cb
Source dataset
uspto-grants-2002_11
Patent number
US06475347B1

Reaction notes

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