Veratrole → 1-(6-Bromohexyl)-2,3-dimethoxybenzene

HRID 1613036Notes

Reaction equation

HRID 1613036 reaction equation
C([Li])CCC.CCCCCC.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]Br>O1CCCC1>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH3:12])[C:15]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 7043VeratroleHCID 8058HexaneHCID 123681,6-DibromohexaneHCID 178418339Butyllithium

Product 1

HCID 149862831-(6-Bromohexyl)-2,3-dimethoxybenzeneYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.55M butyl lithium in hexane (195 mL, 0.3 mol) was added dropwise over 30 minutes to a stirred solution of 1,2-dimethoxybenzene (41.4 g, 0.3 mol) in 700 mL of anhydrous tetrahydrofuran at room temperature under argon. The reaction mixture was stirred and heated at 40° for 4 hours and then cooled to -70°. A solution of 46 mL (0.3 mol) of 1,6-dibromohexane in 250 mL of anhydrous tetrahydrofuran was added dropwise over 30 minutes. The cooling bath was removed and the reaction mixture was stirred for 1 hour and then heated at 40° for 4 hours. Most of the solvent was removed, 90 mL of 3NHCl was added and the product was extracted with hexane. The extract was washed with sodium bicarbonate solution, dried and concentrated under reduced pressure to yield an oil. Distillation gave 1-(6-bromohexyl)-2,3-dimethoxybenzene as a yellow oil (29 g, 32% yield, b.p. 125°-140°/0.15 mm).

Workup

  1. temperatureheated at 40° for 4 hours
  2. temperaturecooled to -70°
  3. customThe cooling bath was removed
  4. stirringthe reaction mixture was stirred for 1 hour
  5. temperatureheated at 40° for 4 hours
  6. customMost of the solvent was removed
  7. addition90 mL of 3NHCl was added
  8. extractionthe product was extracted with hexane
  9. washThe extract was washed with sodium bicarbonate solution
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customto yield an oil
  13. distillationDistillation

Sources & evidence

ORD record
ord-d29dd8591873488d97acc160e9c2695a
Source dataset
uspto-grants-1993_03
Patent number
US05191108

Reaction notes

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