Benzyl Bromide → 1-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzene

HRID 2108251Notes

Reaction equation

HRID 2108251 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[C:9]=1O.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](=[O:27])([O-])[O-].[K+].[K+].COCCOCCN(CCO[CH2:48][CH2:49]OC)CCOCCOC>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]=1[O:27][CH2:24][C:49]1[CH:48]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 149862841-(6-Bromohexyl)-2,3-dihydroxybenzene

Product 1

HCID 149864341-(6-Bromohexyl)-2,3-bis(phenylmethoxy)benzeneYield 561.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 31.3 g (0.115 mol) of 1-(6-bromohexyl)-2,3-dihydroxybenzene, 41 mL (0.34 mol) of benzyl bromide, 47.5 g (0.34 mol) of potassium carbonate and 4.4 mL (13.6 mmol) of tris[2-(2-methoxyethoxy)ethyl]amine (TDA-1) in 750 mL of toluene was stirred at reflux for 40 hours. The reaction mixture was washed with half-saturated brine, dried and concentrated under reduced pressure to which was purified by HPLC using 25% toluene-hexane to give 34.6 g (67% yield) of 1-(6-bromohexyl)-2,3-bis(phenylmethoxy)benzene as an oil.

Workup

  1. temperatureat reflux for 40 hours
  2. washThe reaction mixture was washed with half-saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure to which
  5. customwas purified by HPLC

Sources & evidence

ORD record
ord-b57bd7ddc66041cb975fc8b9473ee627
Source dataset
uspto-grants-1990_06
Patent number
US04937373

Reaction notes

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