Benzyl Bromide → Benzene, [[(12-bromododecyl)oxy]methyl]-

HRID 1289397Notes

Reaction equation

HRID 1289397 reaction equation
[H-].[Na+].O1CCCC1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 13789512-Bromo-1-dodecanol

Product 1

HCID 11100339Benzene, [[(12-bromododecyl)oxy]methyl]-Yield 65.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent

Procedure

First, 2.4 g of 60% sodium hydride and 100 ml of dry tetrahydrofuran were placed in a 300 ml flask whose content was replaced with argon. Then, 15 ml of a tetrahydrofuran solution containing 11.3 g of benzyl bromide, 15 ml of a tetrahydrofuran solution containing 15.9 g of 12-bromododecanol, and 0.1 g of tetrabutylammonium iodide were added to the reaction mixture. The resultant reaction mixture was stirred under reflux for 2.5 hours. The reaction mixture was poured into water, and an organic layer was extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/3) to obtain 14.0 g of 1-bromo-12-benzyloxydodecane (Y: 65.7%). The compound thus obtained had a purity of 98.4% by GC.

Workup

  1. additionwere added to the reaction mixture
  2. customThe resultant reaction mixture
  3. temperatureunder reflux for 2.5 hours
  4. extractionan organic layer was extracted with toluene
  5. washThe toluene layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/3)

Sources & evidence

ORD record
ord-3ef41b2ced21489787fd31b062ee24c3
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Reaction notes

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