Ethanol → 2-(1-Methylcyclohexyl)-4-bromoanisole

HRID 860567Notes

Reaction equation

HRID 860567 reaction equation
[CH3:1][C:2]1([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[OH:15])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[C:16]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O.CCO>CC(C)=O.CCOCC.O>[CH3:1][C:2]1([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=2[O:15][CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

8

Reactant 4

HCID 702EthanolHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 105638754-Bromo-2-(1-methylcyclohexyl)phenol

Product 1

HCID 106843592-(1-Methylcyclohexyl)-4-bromoanisoleYield 44%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 2-(1-methylcyclohexyl)-4-bromophenol (29.68 g, 0.110 mol) and K2CO3 (30.48 g, 0.221 mol) in 200 mL of anhydrous acetone was added a neat solution of dimethylsulfate (13.91 g, 0.110 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 the residue distilled under reduced vacuum, 130–132° C. (0.7 mm/Hg). The impure fractions were combined and further purified on silica gel (hexane) to give a total amount of 2-(1-methylcyclohexyl)-4-bromoanisole as an oil (13.66 g, 44%). 1H NMR (300 MHz, CDCl3): δ 1.26 (s, 3H), 1.30–1.70 (m, 8H), 1.90–2.10 (m, 2H), 3.79 (s, 3H), 6.74 (d, J=8.4 Hz, 1H), 7.26 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.36 (d, J=2.4 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. distillationthe residue distilled under reduced vacuum, 130–132° C. (0.7 mm/Hg)
  7. customfurther purified on silica gel (hexane)

Sources & evidence

ORD record
ord-c38e29321d9b4aa88dcf0e701cab449a
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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