tert-Butanol → HCID 54047863, compound

HRID 1769212Notes

Reaction equation

HRID 1769212 reaction equation
[CH3:1][C:2]([N:13]=[C:14]=[O:15])([CH3:12])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([CH3:11])=[CH2:10])[CH:4]=1.[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17]>CC(C)([O-])C.[K+].CCCCCC>[C:16]([O:20][C:14](=[O:15])[NH:13][C:2]([CH3:1])([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([CH3:11])=[CH2:10])[CH:4]=1)[CH3:12])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 6386tert-ButanolHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene

Product 1

HCID 54047863HCID 54047863, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23665647Potassium tert-butoxideCatalystHCID 8058HexaneSolvent

Procedure

Into a 3-neck, 10 L round bottom flask equipped with a mechanical stirrer, condenser, and a nitrogen inlet was placed α,α-dimethyl-m-isopropenylbenzyl isocyanate (1083 g, 5.38 mol), hexane (6 L), and t-butyl alcohol (398.8 g, 5.38 mol). While the mixture was stirred at room temperature, potassium t-butoxide (18.0 g, 160 mmol) was added in portions. Throughout the addition the reaction temperature increased to 50° C. The reaction was complete within an hour. The reaction mixture was washed with water (5 L), and thereafter, the organics were separated from the aqueous layer. The organics were dried over magnesium sulfate, filtered, and evaporated to yield a yellow-brown semi-solid. Recrystallization from hexane afforded essentially pure {1-methyl-1-[3-(1-methylethenyl)phenyl]ethyl}carbamic acid t-butyl ester (1193 g, 81% isolated yield), as shown by proton and carbon-13 NMR spectroscopy.

Workup

  1. customInto a 3-neck, 10 L round bottom flask equipped with a mechanical stirrer, condenser, and a nitrogen inlet
  2. additionThroughout the addition the reaction temperature
  3. temperatureincreased to 50° C
  4. waitThe reaction was complete within an hour
  5. washThe reaction mixture was washed with water (5 L)
  6. customthe organics were separated from the aqueous layer
  7. dry with materialThe organics were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto yield a yellow-brown semi-solid
  11. customRecrystallization from hexane

Sources & evidence

ORD record
ord-06df3f3fd645475bb73c8dc050d397db
Source dataset
uspto-grants-1995_01
Patent number
US05380796

Reaction notes

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