Ethanol → tert-Butylanisole

HRID 860560Notes

Reaction equation

HRID 860560 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:12]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O.CCO>CC(C)=O.CCOCC.O>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 69232-Tert-ButylphenolHCID 11430Potassium Carbonate

Product 1

HCID 270626tert-ButylanisoleYield 78%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 2-t-butylphenol (20.00 g, 0.133 mol) and K2CO3 (36.80 g, 0.266 mol) in 260 mL of anhydrous acetone was added a neat solution of dimethylsulfate (17.63 g, 0.140 mol) dropwise through a syringe over 5 minute at RT under argon. The resulting thick suspension was stirred over night at RT and 100 mL of EtOH was added. After 1 hour, the mixture was diluted with ether and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine and dried with MgSO4. After filtration, the solvents were removed and dried under high vacuum to give afford 2-t-butylanisole (16.99 g, 78% yield). 1H NMR (300 MHz, CDCl3): δ 1.40 (s, 9H), 3.86 (s, 3H), 6.88–6.96 (m, 2H), 7.18–7.26 (m, 1H), 7.31 (dd, J1=7.5 Hz, J2=1.2 Hz, 1H).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried with MgSO4
  4. filtrationAfter filtration
  5. customthe solvents were removed
  6. customdried under high vacuum
  7. customto give

Sources & evidence

ORD record
ord-1e85675fef6a4618875ab635b878b96e
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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