2-Bromopropane → 2,3-Dimethyl-1-(2-propyl)oxybenzene

HRID 1267166Notes

Reaction equation

HRID 1267166 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH:17]([CH3:19])[CH3:18]>CC(C)=O>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 106872,3-DimethylphenolHCID 11430Potassium Carbonate

Product 1

HCID 203083562,3-Dimethyl-1-(2-propyl)oxybenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution/suspension of 2,3-dimethylphenol (10 g) and potassium carbonate (6.8 g) in acetone (150 ml) at reflux was added 2-bromopropane (46 ml) drop-wise over 30 min. The solution was heated at reflux for 4 days. After cooling, the solvent was evaporated and the residue was dissolved in ether and water. The ether phase was separated and was worked up according to the general procedure. Column chromatography on silica gel (eluent: ethyl acetate/heptane 1:19) afforded pure 2,3-dimethyl-1-(2-propyl)oxybenzene (13.2 g) as a mobile, slightly brown oil which was used without further purification.

Workup

  1. temperatureat reflux
  2. temperatureThe solution was heated
  3. temperatureat reflux for 4 days
  4. temperatureAfter cooling
  5. customthe solvent was evaporated
  6. dissolutionthe residue was dissolved in ether
  7. customThe ether phase was separated

Sources & evidence

ORD record
ord-11f416f3a15c48d8b4b46de6712b45f2
Source dataset
uspto-grants-2003_04
Patent number
US06552044B2

Reaction notes

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