Ammonia → 3-tert-Butyltoluene

HRID 2038033Notes

Reaction equation

HRID 2038033 reaction equation
N.P(OCC)(OCC)(O[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[C:12]([CH3:15])([CH3:14])[CH3:13])=O.[Li]>CCOCC>[C:12]([C:6]1[CH:5]=[CH:10][CH:9]=[C:8]([CH3:11])[CH:7]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 3028194LithiumHCID 591293942-Tert-butyl-4-methylphenyl diethyl phosphate

Product 1

HCID 337113-tert-Butyltoluene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To NH3(liquid, 1000 mL) was added a solution of 2-tert-butyl-4-methylphenyl diethyl phosphate (60 g, crude from last step, about 0.2 mol) in Et2O (anhydrous, 500 mL) at −78° C. under N2 atmosphere. Lithium metal was added to the solution in small pieces until the blue color persisted. The reaction mixture was stirred at −78° C. for 15 min and then was quenched with sat. NH4Cl until the mixture turned colorless. Liquid NH3 was evaporated and the residue was dissolved in water. The mixture was extracted with Et2O (400 mL×2). The combined organics were dried over Na2SO4 and evaporated to give 1-tert-butyl-3-methylbenzene

Workup

  1. customwas quenched with sat. NH4Cl until the mixture
  2. customLiquid NH3 was evaporated
  3. dissolutionthe residue was dissolved in water
  4. extractionThe mixture was extracted with Et2O (400 mL×2)
  5. dry with materialThe combined organics were dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-8125273b30064ed29c1001a15f965918
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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