2,5-Dimethylphenol → 2-(2-bromoethoxy)-1,4-dimethylbenzene

HRID 2299230Notes

Reaction equation

HRID 2299230 reaction equation
[Br:1][CH2:2][CH2:3]Br.[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:7]=1[OH:13].C[O-].[Na+]>C(O)C>[Br:1][CH2:2][CH2:3][O:13][C:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=1[CH3:5]

Participants

5

Reactant 3

HCID 72672,5-DimethylphenolHCID 78391,2-DibromoethaneHCID 10942334Sodium Methoxide

Product 1

HCID 36767422-(2-bromoethoxy)-1,4-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of 75.2 g (0.4 mol) 1,2-dibromoethane in 80 mL of anhydrous ethanol was stirred and heated to 65° C. under a nitrogen atmosphere, and then a solution of 24.4 g (0.2 mol) of 2,5-dimethylphenol and 10.8 g (0.2 mol) of NaOMe in anhydrous ethanol (100 mL) was added into the above solution dropwise. After finish adding, refluxed for 5 hours. The mixture was cooled to room temperature, washed and extract d with ethyl ether, 2M NaOH solution and deionized water. The organic phase was collected, dried with CaCl2 and then filtered. After evaporating the solvent from the filtrate, 1-(2′-bromoethanoxy) 2,5-dimethylbenzene was purified by vacuum distillation. 1H-NHR (CDCl3, ppm): δ 7.00 (d, 1H), δ 6.4 (d, 1H), δ 6.6 (s, 1H), δ 4.24 (t, 2H), δ 3.62 (t, 2H), δ 2.3 (s, 3H), δ 2.2 (s, 3H).

Workup

  1. additionAfter finish adding
  2. temperaturerefluxed for 5 hours
  3. temperatureThe mixture was cooled to room temperature
  4. washwashed
  5. extractionextract
  6. customThe organic phase was collected
  7. dry with materialdried with CaCl2
  8. filtrationfiltered
  9. customAfter evaporating the solvent from the filtrate, 1-(2′-bromoethanoxy) 2,5-dimethylbenzene
  10. distillationwas purified by vacuum distillation

Sources & evidence

ORD record
ord-d7f44e05d94a4094bf5ac3220b4a6742
Source dataset
uspto-grants-2002_12
Patent number
US06495644B1

Reaction notes

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