Water → 1-Bromo-4-(2-propoxyethoxy)benzene

HRID 413599Notes

Reaction equation

HRID 413599 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH:7](O)[CH3:8])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH3:15].[OH-:16].[Na+].O>CCCC[N+](CCCC)(CCCC)CCCC.S([O-])(O)(=O)=O.CS(C)=O.O1CCCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:16][CH2:13][CH2:14][CH3:15])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 78401-BromopropaneHCID 14798Sodium HydroxideHCID 18533386p-Bromophenoxyethanol

Product 1

HCID 185333961-Bromo-4-(2-propoxyethoxy)benzeneYield 98%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 679Dimethyl SulfoxideSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

p-Bromophenoxyethanol (2067 g, 9.5227 mol), bromopropane (2342 g, 19.05 mol) and tetrabuthylammonium hydrogensulfate (162 g, 0.476 mol) were dissolved in 10.3 L of dimethyl sulfoxide. A 50 W/W% aqueous sodium hydroxide solution (3.81 kg, 47.625 mol) was dropped slowly. Since heat was generated, the dropping rate and the external temperature were adjusted so that the internal temperature was kept at 40-50° C. After cooling and stirring for 1.5 hours, the mixture was cooled to 20-30° C. and 20.6 L of water was added at that temperature. After addition of 15.5 L of toluene and 4 L of tetrahydrofuran, phase separation was conducted. To the water layer, 5.2 L of toluene 5.2 L and t1.3 L of tetrahydrofuran and extraction was conducted. The organic layers were combined and washed with 20.6 L of water, two 10.3-L portions of 20% brine, two 20.6-L portions of water. After vacuum concentration, the residue was distilled under reduced pressure (135-155° C. /5 mmHg) to yield 2412.8 g (Yield 98%) of 1-p-bromophenoxy-2-propoxyethane as a colorless oily matter.

Workup

  1. temperatureSince heat
  2. customwas kept at 40-50° C
  3. temperatureAfter cooling
  4. extractionTo the water layer, 5.2 L of toluene 5.2 L and t1.3 L of tetrahydrofuran and extraction
  5. washwashed with 20.6 L of water, two 10.3-L portions of 20% brine, two 20.6-L portions of water
  6. concentrationAfter vacuum concentration
  7. distillationthe residue was distilled under reduced pressure (135-155° C. /5 mmHg)

Sources & evidence

ORD record
ord-76970cd7caf84098a9fb10d41749db76
Source dataset
uspto-grants-2003_05
Patent number
US06566535B1

Reaction notes

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